Water → HCID 86699760, 화합물

HRID 515195노트

반응식

HRID 515195 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:26])[C:11]2[C:16]([O:17]C)=[CH:15][C:14]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:13][C:12]=2[F:25])=[CH:4][CH:3]=1.B(Br)(Br)Br.O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:26])[C:11]2[C:16]([OH:17])=[CH:15][C:14]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[CH:13][C:12]=2[F:25])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 25134Boron tribromideHCID 86699759HCID 86699759, 화합물

생성물 1

HCID 86699760HCID 86699760, 화합물수율 39%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of N-[(4-chlorophenyl)-methyl]-2-fluoro-6-methoxy-4-morpholin-4-yl-benzamide (1.3 g, 3.44 mmol) in dichloromethane (40 ml) is added neat boron tribromide (0.82 ml, 8.6 mmol) at −78° C. The temperature is raised to room temperature over a period of 2 h. The reaction mixture is poured onto cold water, extracted with dichloromethane (3×50 ml). The combined organic layers are washed with brine (30 ml), dried over sodium sulfate and evaporated to dryness. The crude product is purified by column chromatography (silica gel, 5% ethyl acetate/dichloromethane) to yield N-[(4-chlorophenyl)-methyl]-2-fluoro-6-hydroxy-4-morpholin-4-yl-benzamide (0.5 g, 1.3 mmol, 39%).

후처리

  1. extractionextracted with dichloromethane (3×50 ml)
  2. washThe combined organic layers are washed with brine (30 ml)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude product is purified by column chromatography (silica gel, 5% ethyl acetate/dichloromethane)

출처 및 근거

ORD 기록
ord-da761453e3c649cda78384de83998872
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108936B2

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