Cesium carbonate → 7-chloro-6-[4-(2-methyl-butyl)-benzylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 2041559ノート

反応式

HRID 2041559 の反応式
[CH3:1][CH:2]([CH2:12][CH3:13])[CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1.[Cl:14][C:15]1[CH:31]=[CH:30][C:18]2[CH2:19][CH2:20][N:21]([C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[CH2:22][CH2:23][C:17]=2[C:16]=1OS(C(F)(F)F)(=O)=O.C1C=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+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:31]=[CH:30][C:18]2[CH2:19][CH2:20][N:21]([C:24](=[O:29])[C:25]([F:26])([F:28])[F:27])[CH2:22][CH2:23][C:17]=2[C:16]=1[NH:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][CH:2]([CH3:1])[CH2:12][CH3:13])=[CH:11][CH:10]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 576561404-(2-Methyl-butyl)-benzylamine

生成物 1

HCID 866296917-chloro-6-[4-(2-methyl-butyl)-benzylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine収率 59%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
95 °C

実験手順

Under a nitrogen atmosphere, add 4-(2-methyl-butyl)-benzylamine (450 mg, 2.54 mmol), 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (720 mg, 1.7 mmol), palladium(II) acetate (40 mg, 0.17 mmol), BINAP (222 mg, 0.34 mmol) and cesium carbonate (1.4 g, 4.3 mmol) to toluene (20 mL). Heat the mixture at 95° C. for 12 h. Cool the mixture to room temperature and apply the mixture to a silica gel column eluting with hexane/EtOAc (10:1) to provide 7-chloro-6-[4-(2-methyl-butyl)-benzylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (450 mg, 59%). MS (ES+) m/z: 453 (M+H)+.

後処理

  1. temperatureCool the mixture to room temperature
  2. washapply the mixture to a silica gel column eluting with hexane/EtOAc (10:1)

出典と根拠

ORDレコード
ord-af23f83ebcf34e6bbc02342f8467af57
出典データセット
uspto-grants-2013_11
特許番号
US08580780B2

反応ノート

読み込み中…