Cesium fluoride → N-(3,5-Bis-trifluoromethyl-benzyl)-N-(9-methyl-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide

HRID 2353918노트

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HRID 2353918 반응식
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([CH:11]1[CH2:17][CH2:16][CH2:15][NH:14][C:13]2[C:18](Br)=[CH:19][C:20]([C:22]([F:25])([F:24])[F:23])=[CH:21][C:12]1=2)[C:8](=[O:10])[CH3:9].[CH3:36]B(O)O.[F-].[Cs+]>O1CCOCC1>[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([CH:11]1[CH2:17][CH2:16][CH2:15][NH:14][C:13]2[C:18]([CH3:36])=[CH:19][C:20]([C:22]([F:25])([F:24])[F:23])=[CH:21][C:12]1=2)[C:8](=[O:10])[CH3:9]

참가 물질

5

반응물 3

HCID 25953Cesium fluorideHCID 139377Methylboronic AcidHCID 86616074N-(3,5-Bis-trifluoromethyl-benzyl)-N-(9-bromo-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide

생성물 1

HCID 86616073N-(3,5-Bis-trifluoromethyl-benzyl)-N-(9-methyl-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide수율 63%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

A mixture of N-(3,5-Bis-trifluoromethyl-benzyl)-N-(9-bromo-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide (0.0830 g, 0.144 mmol), methyl boronic acid (0.0260 g, 0.432 mmol) and cesium fluoride (0.0770 mg, 0.504 mmol) in dioxane (2.00 ml) was purged with nitrogen for 10 minutes. To it was added PdCl2(dppf) (0.0170 g) in one portion. The mixture was heated at 80° C. overnight. The solid was removed by filtration, washed with ethyl acetate (30.0 ml) and the filtrate was concentrated in vacuo. Purification by silica gel chromatography (gradient eluent, 0-40% ethyl acetate in hexane) provided the titled compound (0.0460 g, 63%) as white solid. MS (ES+): 513 (M+H).

후처리

  1. customwas purged with nitrogen for 10 minutes
  2. additionTo it was added PdCl2(dppf) (0.0170 g) in one portion
  3. customThe solid was removed by filtration
  4. washwashed with ethyl acetate (30.0 ml)
  5. concentrationthe filtrate was concentrated in vacuo
  6. customPurification by silica gel chromatography (gradient eluent, 0-40% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-8a8553be79fd42ebae2157c49f45195b
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07749992B2

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