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

反応式

HRID 68740 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 21735183Dimethylformamide toluene溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-988177dc72a240a68ef7f7ee98d29c80
出典データセット
uspto-grants-2014_09
特許番号
US08822447B2

関連ノート

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