N-bromobutanimide → 8-Bromo-6-[(4-tert-butylphenyl)sulfonyl]-7-methyl-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

HRID 1691441

反応式

HRID 1691441 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:20]3[C:21]([CH3:25])=[CH:22][CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:26]=[C:27]([C:30]([F:33])([F:32])[F:31])[CH:28]=[CH:29][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:41])C(=O)C1>ClCCl.C(#N)C>[Br:41][C:22]1[CH:23]=[CH:24][C:19]2[NH:18][C:17]3[N:26]=[C:27]([C:30]([F:32])([F:33])[F:31])[CH:28]=[CH:29][C:16]=3[CH2:15][N:14]([S:11]([C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=3)(=[O:12])=[O:13])[C:20]=2[C:21]=1[CH3:25]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 669017496-(4-Tert-butylphenyl)sulfonyl-7-methyl-2-(trifluoromethyl)-5,11-dihydropyrido[3,2-c][1,5]benzodiazepine

生成物 1

HCID 669017308-Bromo-6-[(4-tert-butylphenyl)sulfonyl]-7-methyl-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
5 °C

実験手順

To a solution of the product of Step C (0.95 g, 2 mmol mol) in dichloromethane (5 ml) and acetonitrile (50 ml) was added NBS (0.35 g, 2 mmol mol) in portions at 0° C. After stirring at 5° C. for 12 h, the reaction mixture was concentrated, and the residue was partitioned between dichloromethane and water. The organic layer was separated, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound. 1H NMR (400 MHz, CDCl3) δ 7.50 (d, J=7.2 Hz, 1H), 7.40 (d, J=8.4 Hz, 1H), 7.13 (m, 5H), 6.52 (m, 2H), 5.20 (d, J=16.8 Hz, 1H), 4.34 (d, J=16.8 Hz, 1H), 2.65 (s, 3H), 1.24 (s, 9H).

後処理

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was partitioned between dichloromethane and water
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-408aa878a081433a823fbef3b6ebb9fd
出典データセット
uspto-grants-2012_04
特許番号
US08153626B2

関連ノート

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