.MS(ESI)m/z: 386.14(C2iHi8F3N3〇,[M+H] + ) .Anal .Calcd for C2IHisF3N3O:C,65.45 ;H, 4.71;N,10.90.Found:C,65.31;H,4.70 ;N,10.87.
[0038] 實(shí)施例八:l-(5_(5-甲氧基-I-甲基-IH-吲哚-3-基)-3_苯基-4,5-二氫-lH-吡唑-1-基)乙酮(6h)的制備
[0040] 制備方法參考實(shí)施例一。Yield:45.0% .m.p. 175~net.1!! NMR(DMS〇-d6, 400ΜΗζ)δ:7.93-7·79(m,2H),7·56-7.42(m,3H),7.29(d,J=8.8Hz,lH),7.20(s,lH),6·80 (s,lH),6.77(d,J = 8.8Hz,lH),5.78(dd,J=11.7,3.8Hz,lH),3.82(dd,J=17.9,11.7Hz, lH),3.68(s,3H),3.54(s,3H),3.25(dd,J=17.9,3.9Hz,lH),2.26(s,3H).MS(ESI)m/z: 348.16(C2iH2iN 3〇2,[M+H] + ).Anal.Calcd for C2iH2iN3〇2:C,72.60;H,6.09;N,12.10.Found: C,72.71;H,6.10;N,12.12.
[0041] 實(shí)施例九:丨-"-"-甲氧基-甲基-1H-吲哚-3-基)-3-( 4-甲氧基苯基)-4,5-二 氫-1H-吡唑-1-基)乙酮(6i)的制備
[0043] 制備方法參考實(shí)施例一。Yield:46.7% .m.p. 158~IeOaC-1H NMR(DMS〇-d6, 400MHz)S:7.78(d,J = 8.8Hz,2H),7.28(d,J = 8.8Hz,lH),7.18(s,lH),7.03(d,J = 8.9Hz, 2H),6.81(s,lH),6.77(d,J = 8.8Hz,lH),5.75(dd,J=11.6,3.8Hz,lH),3.84-3.69(m,4H), 3.68(s,3H),3.56(s,3H),3.21(dd,J=17.8,3.9Hz,lH),2.23(s,3H).MS(ESI)m/z:378.17 (C22H23N3O3,[M+H] + )· Anal · Cal cd for C22H23N3O3 :C,70.01;H,6.14;N,11.13. Found: C, 69·91;Η,6·16;Ν,11·13·
[0044] 實(shí)施例十:1-(3-(3, 4-二甲氧基苯基)-5-(5-甲氧基-1-甲基- 1!1-吲哚-3-基)-4, 5-二氫-IH-吡唑-1-基)乙酮(6j)的制備
[0046] 制備方法參考實(shí)施例一。Yield: 10.2% .m.p. 186~ISTqC-1H NMR(DMS〇-d6, 400MHz)S:7.42(s,lH),7.34(d,J = 8.3Hz,lH),7.29(d,J = 8.8Hz,lH),7.17(s,lH),7.03 (d,J = 8.4Hz,lH),6.83(s,lH),6.78(d,J = 8.8Hz,lH),5.76(dd,J=ll ·5,3·4Ηζ,1Η), 3.86-3.72(m,7H),3.68(s,3H),3.58(s,3H),3.24(dd,J=17.7,3.6Hz,lH),2.25(s,3H).MS (ESI )m/z : 408 · 18 (C23H25N3O4,[M+H] +) · Anal · Cal cd for C23H25N3O4: C,67 · 80 ; H,6 · 18; N, 10.31.Found:C,67.93;H,6.17;N,10.32.
[0047] 實(shí)施例^^一:l-(3-(4-氟苯基)-5_(5-甲氧基-I-甲基-IH-吲哚-3-基)-4,5_二氫-IH-吡唑-1-基)乙酮(6k)的制備
[0049] 制備方法參考實(shí)施例一。Yield:29.8% .m.p. 178~ISO0C-1H NMR(DMS〇-d6, 400MHz)S:7.90(dd,J = 8.7,5.5Hz,2H),7.31(dd,J=18.0,8.9Hz,3H),7.19(s,lH),6.85-6.73(m,2H),5.78(dd,J=11.7,3.8Hz,lH),3.82(dd,J=17.9,11.8Hz,lH),3.68(s,3H), 3.57(s,3H),3.25(dd,J=17.9,3.9Hz,lH),2.25(s,3H) .MS(ESI)m/z:366.15(C2iH2〇FN3〇2, [M+H]+).Anal.Calcd for C2iH2〇FN3〇2:C,69.03;H,5.52;N,11.50.Found :C,69.31;H,5.51; Ν,11·48·
[0050] 實(shí)施例十二:^3-G-氯苯基)-5-(5-甲氧基4-甲基-1H-吲哚- 3-基)-4,5-二氫-IH-吡唑-1-基)乙酮(61)的制備
[0052]制備方法參考實(shí)施例一。Yield:36.7% .m.p. 169~HOqC-1H NMR(DMS〇-d6, 400MHz)S:7.86(d,J = 8.6Hz,2H),7.55(d,J = 8.6Hz,2H),7.29(d,J = 8.6Hz,lH),7.20(s, lH),6.78(d,J = 8.7Hz,2H),5.79(dd,J=11.7,3.9Hz,lH),3.81(dd,J=18.0,11.8Hz,lH), 3.68(s,3H),3.57(s,3H),3.24(dd,J=17.9,4.0Hz,lH),2.25(s,3H).MS(ESI)m/z:382.12 (C21H20CIN3O2,[M+H] +) · Anal · Calcd for C21H20CIN3O2: C,66 · 05; H,5 · 28; N,11 · 00 · Found: C, 65·98;Η,5·27;Ν,10·98·
[0053] 實(shí)施例十三:l-(3-(4-溴苯基)-5-(5-甲氧基-I-甲基-IH-吲哚-3-基)-4,5-二氫-IH-吡唑-1-基)乙酮(6m)的制備
[0055]制備方法參考實(shí)施例一。Yield:38.6% .m.p. 172~HS0C-1H NMR(DMS〇-d6, 400MHz)S:7.78(d,J = 8.5Hz,2H),7.68(d,J = 8.4Hz,2H),7.29(d,J = 8.5Hz,lH),7.19(s, lH),6.78(d,J = 8.6Hz,2H),5.79(dd,J=11.7,3.9Hz,lH),3.81(dd,J=18.0,11.9Hz,lH), 3.68(s,3H),3.58(s,3H),3.24(dd,J=18.0,4.0Hz,lH),2.25(s,3H).MS(ESI)m/z:426.07 (C2IH20BrN3O2, [M+H]+).Anal.Calcd for C2IH20BrN3O2:C,59.17;H,4.73;N,9.86.Found:C, 59·33;Η,4·71;Ν,9·85·
[0056] 實(shí)施例十四:l-(5-(5-溴-I-甲基-IH-吲哚-3-基)-3-苯基-4,5-二氫-IH-吡唑-1-基)乙酮(6n)的制備
[0058]制備方法參考實(shí)施例一。Yield:59.0% .m.p. 173~HfC-1H NMR(DMS〇-d6, 400MHz)S:7.94-7.74(m,2H),7.61(s,lH),7.57-7.41(m,3H),7.39(d,J=8.7Hz,lH),7.29 (s,lH),7.25(d,J = 8.7Hz,lH),5.81(dd,J=11.7,4.2Hz,lH),3.84(dd,J=18.0,11.8Hz, 1H),3.72(s,3H),3.25(dd,J=18.0,4.3Hz,lH),2.27(s,3H).MS(ESI)m/z:396.06 (C 20HisBrN3O,[M+H] + )·Anal ·Calcd for C20HisBrN3O:C,60·62;Η,4·58;Ν,10.60.Found:C, 60·79;Η,4·57;Ν,10·63·
[0059] 實(shí)施例十五:l-(5-(5-溴-I-甲基-IH-吲哚-3-基)-3-(2-甲氧基苯基)-4,5-二氫-IH-吡唑-1-基)乙酮(6〇)的制備
[0061] 制備方法參考實(shí)施例一。Yield:58.5% .m.p. 180~ISIqC^1H NMR(DMS〇-d6, 400MHz)S:7.85(d,J = 6.1Hz,lH),7.63(s,lH),7.46(t,J = 7.0Hz,lH),7.39(d,J = 8.7Hz, lH),7.30(s,lH),7.25(d,J = 6.9Hz,lH),7.14(d,J = 8.3Hz,lH),7.06(t,J = 7.9Hz,lH), 5.74(dd,J=11.8,4.2Hz,lH),3.88(dd,J=18.5,11.8Hz,lH),3.81(s,3H),3.73(s,3H), 3.28(dd,J=18.5,4.2Hz,lH),2.23(s,3H) .MS(ESI)m/z:426.07(C2iH2()BrN3〇2, [M+H] + ) .Anal.Calcd for C2iH2〇BrN3〇2:C,59.17;H,4.73;N,9.86.Found:C,59.31;H,4.74;N,9.84.
[0062] 實(shí)施例十六:U5-G-溴-卜甲基-1H-吲哚-3-基)-3-( 3-甲氧基苯基)-4,5-二氫― 1H-吡唑-1-基)乙酮(6p)的制備
[0064]制備方法參考實(shí)施例一。Yield:59.9% .m.p. 184~ISSqC^1H NMR(DMS〇-d6, 400MHz)S:7.60(s,lH),7.44-7.36(m,3H),7.34(s,lH),7.29(s,lH),7.26(d,J=6.9Hz, lH),7.11-7.02(m,lH),5.80(dd,J=11.7,4.3Hz,lH),3.89-3.78(m,4H),3.72(s,3H),3.26 (dd,J=18.0,4.3Hz,1H),2.27(s,3H).MS(ESI)m/z:426.07(C 2IH20BrN3O2, [M+H] + ) .Anal.Calcd for C2iH2〇BrN3〇2:C,59.17;H,4.73;N,9.86.Found:C,59.24;H,4.72;N,9.87.
[0065] 實(shí)施例十七:l-(5_(5-溴-I-甲基-IH-吲哚-3-基)-3_(4-甲氧基苯基)-4,5_二氫-1H-吡唑-1-基)乙酮(6q)的制備
[0067]制備方法參考實(shí)施例一。丫161(1:75.8%.111.?.208~209°(3.111麗1?(0150-(16, 400MHz)S:7.77(d,J = 8.8Hz,2H),7.59(s,lH),7.39(d,J = 8.7Hz,lH),7.28(s,lH),7.25 (d,J = 7.0Hz,lH),7.03(d,J = 8.8Hz,2H),5.77(dd,J= 11.6,4· IHz,1Η),3 ·91-3·75(ι?, 4H),3.72(s,3H),3.21(dd,J=17.9,4.2Hz,lH),2.25(s,3H).MS(ESI)m/z:426.07 (C 2IH20BrN3O2, [M+H]+).Anal.Calcd for C2IH20BrN3O2:C,59.17;