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 2041559노트

반응식

HRID 2041559 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

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온도
95 °C

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-af23f83ebcf34e6bbc02342f8467af57
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580780B2

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