Cesium carbonate → 6-[4-(3,5-dimethyl-piperazin-1-yl)-phenyl]-3-ethyl-4-methoxy-1-phenyl-1H-pyrazolo[3,4-b]pyridine

HRID 68740

반응식

HRID 68740 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13](C)[C:12]3[N:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:16]=[C:17]([CH2:18][CH3:19])[C:11]=3[C:10](=[O:26])[CH:9]=2)=[CH:4][CH:3]=1.[CH3:27][CH:28]1[CH2:33][NH:32][CH2:31][CH:30]([CH3:34])[NH:29]1.[CH:35]1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH3:34][CH:30]1[NH:29][CH:28]([CH3:27])[CH2:33][N:32]([C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:13]=[C:12]4[N:15]([C:20]5[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:16]=[C:17]([CH2:18][CH3:19])[C:11]4=[C:10]([O:26][CH3:35])[CH:9]=3)=[CH:6][CH:7]=2)[CH2:31]1

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 660562,6-DimethylpiperazineHCID 634876Binap, (A+-)-HCID 674488196-(4-bromophenyl)-3-ethyl-7-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4(7H)-one

생성물 1

HCID 584835716-[4-(3,5-dimethyl-piperazin-1-yl)-phenyl]-3-ethyl-4-methoxy-1-phenyl-1H-pyrazolo[3,4-b]pyridine

시약·촉매·용매 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 21735183Dimethylformamide toluene용매

반응 조건

온도
120 °C

실험 절차

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 6-(4-bromophenyl)-3-ethyl-7-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4(7H)-one (100 mg, 0.24 mmol, 1.00 equiv) in toluene/DMF (2 ml/Id), 2,6-dimethylpiperazine (140 mg, 1.23 mmol, 5.01 equiv), BINAP (15.3 mg, 0.02 mmol, 0.10 equiv), Pd2(dba)3 (22.4 mg, 0.02 mmol, 0.10 equiv), Cs2CO3 (140 mg, 0.73 mmol, 2.96 equiv), dppf (9.18 mg). The resulting solution was stirred overnight at 120° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (200:1-100:1) to yield 6-[4-(3,5-dimethyl-piperazin-1-yl)-phenyl]-3-ethyl-4-methoxy-1-phenyl-1H-pyrazolo[3,4-b]pyridine as a yellow solid.

후처리

  1. customInto a 50-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. concentrationThe resulting mixture was concentrated under vacuum

출처 및 근거

ORD 기록
ord-988177dc72a240a68ef7f7ee98d29c80
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822447B2

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