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

HRID 2386902ノート

反応式

HRID 2386902 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0976be45030145459fcf7d4db72742b8
出典データセット
uspto-grants-2012_09
特許番号
US08268843B2

反応ノート

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