Boron tribromide → N-Trifluoroacetyl-7-hydroxy-8-iodo-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 221251노트

반응식

HRID 221251 반응식
[F:1][C:2]([F:21])([F:20])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([I:19])[C:15]([O:17]C)=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].B(Br)(Br)Br>ClCCl>[F:20][C:2]([F:1])([F:21])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([I:19])[C:15]([OH:17])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 22292785N-trifluoroacetyl-8-iodo-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

생성물 1

HCID 22292815N-Trifluoroacetyl-7-hydroxy-8-iodo-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine수율 97.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of N-trifluoroacetyl-8-iodo-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (80 mg, 0.19 mmol) in dichloromethane (3 mL) was treated with BBr3 (0.40 mL of a 1.0M solution in CH2Cl2, 0.40 mmol) and stirred overnight at 20 C. The excess BBr3 was quenched with water and the product mixture was diluted with ether (20 mL), washed with Na2CO3 (10 mL) and brine (10 mL), dried with Na2SO4 and concentrated. Flash chromatography (15% EtOAc in hexane, silica) resulted in 74 mg of a white solid. MS calculated for C13H13F3INO2+H: 400, observed: 400.

후처리

  1. customThe excess BBr3 was quenched with water
  2. additionthe product mixture was diluted with ether (20 mL)
  3. washwashed with Na2CO3 (10 mL) and brine (10 mL)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3083c4b0a19a4fdb8c8016160e89c843
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207158B2

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