Boron tribromide → 4-[2-(5,8-Difluoroquinazolin-4-ylamino)-ethyl]-2-methylphenol

HRID 2386902노트

반응식

HRID 2386902 반응식
[F:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:3]=1[C:4]([NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22]C)=[C:18]([CH3:24])[CH:17]=1)=[N:5][CH:6]=[N:7]2.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:3]=1[C:4]([NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH3:24])[CH:17]=1)=[N:5][CH:6]=[N:7]2

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 59222937(5,8-Difluoroquinazolin-4-yl)-[2-(4-methoxy-3-methylphenyl)-ethyl]-amine

생성물 1

HCID 592229364-[2-(5,8-Difluoroquinazolin-4-ylamino)-ethyl]-2-methylphenol수율 101.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (5,8-difluoroquinazolin-4-yl)-[2-(4-methoxy-3-methylphenyl)-ethyl]-amine (0.86 g, 2.6 mmol) in CH2Cl2 (10 mL) cooled to −50° C., was added 7.8 mL BBr3 (1 M in CH2Cl2, 7.8 mmol). The solution was allowed to warm to room temperature and stirred overnight, and then quenched slowly with methanol. The solvent was removed by rotary evaporation, and the residue was diluted with water and stirred for a few min. The pale yellow solid precipitate was collected by suction filtration, washed with water, and dried in vacuum at 50° C. overnight to give 0.83 g (quantitative yield) of 4-[2-(5,8-difluoroquinazolin-4-ylamino)-ethyl]-2-methylphenol. 1H NMR (d4-DMSO+d6-acetone): δ 9.5-8.5 (m, 3H), 7.97 (m, 1H), 7.61 (m, 1H), 6.99 (s, 1H), 6.91 (d, J=8.1 Hz, 1H), 6.75 (d, J=8.1 Hz, 1H), 3.92 (m, 2H), 2.88 (t, J=7.8 Hz, 2H), 2.11 (s, 3H). LC/MS: 316.04 (M++1). The product was used in the following reaction without further purification. M.P. 244-251° C.

후처리

  1. customquenched slowly with methanol
  2. customThe solvent was removed by rotary evaporation
  3. additionthe residue was diluted with water
  4. stirringstirred for a few min
  5. filtrationThe pale yellow solid precipitate was collected by suction filtration
  6. washwashed with water
  7. customdried in vacuum at 50° C. overnight

출처 및 근거

ORD 기록
ord-0976be45030145459fcf7d4db72742b8
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268843B2

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