Boron tribromide → HCID 22292839、化合物

HRID 221280ノート

反応式

HRID 221280 の反応式
[F:1][C:2]([F:22])([F:21])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:19])[C:15]([O:17]C)=[CH:16][C:8]=2[CH2:7][CH:6]1[CH3:20])=[O:4].B(Br)(Br)Br>ClCCl>[F:21][C:2]([F:1])([F:22])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:19])[C:15]([OH:17])=[CH:16][C:8]=2[CH2:7][CH:6]1[CH3:20])=[O:4]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 22292813N-Trifluoroacetyl-8-bromo-1,4-dimethyl-7-methoxy-2,3,4,5-tetrahydro 1H-3-benzazepine

生成物 1

HCID 22292839HCID 22292839、化合物収率 81.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of N-trifluoroacetyl-8-bromo-1,4-dimethyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine (0.383 g, 1.01 mmol) in dichloromethane (30 mL) was treated with BBr3 (2.35 mL of a 1.0M solution in CH2Cl2, 2.35 mmol) and stirred overnight while warming to 20 C. The excess BBr3 is quenched with water, and the resulting mixture was diluted with ether (100 mL), washed with saturated aqueous Na2CO3 (50 mL) and brine (50 mL), dried with Na2SO4 and concentrated. Flash chromatography (15% EtOAc in hexane, silica) resulted in 0.302 g of a white solid. 1H NMR (400 MHz, CDCl3, mixture of rotamers) d 7.22 (m, 1 H), 6.77 (m, 1 H), 5.34 (s, 1 H), 4.35 (m, 1 H), 3.62 (m, 1 H), 3.24 (m, 1 H), 3.13 (m, 2 H), 2.69 (m, 1 H), 1.31 (m, 3H), 1.22 (m, 3 H).

後処理

  1. temperaturewhile warming to 20 C
  2. customThe excess BBr3 is quenched with water
  3. additionthe resulting mixture was diluted with ether (100 mL)
  4. washwashed with saturated aqueous Na2CO3 (50 mL) and brine (50 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-7454b1fff2104b769a76b7dde6a815e5
出典データセット
uspto-grants-2012_06
特許番号
US08207158B2

反応ノート

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