Benzoyl chloride, 3-bromo- → 10-(3-Bromobenzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 2244225Notes

Reaction equation

HRID 2244225 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][CH2:6][C:5]=12.C(N(CC)C(C)C)(C)C.[Br:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=[O:29]>ClCCl>[Br:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28]([N:7]1[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[CH2:10][N:4]2[CH:3]=[CH:2][CH:1]=[C:5]2[CH2:6]1)=[O:29]

Participants

5

Reactant 3

HCID 74377Benzoyl chloride, 3-bromo-HCID 81531DiisopropylethylamineHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 6868783410-(3-Bromobenzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepineYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (5.0 g, 27 mmol) and N,N-diisopropylethylamine (7.5 mL, 43 mmol) in dry dichloromethane (135 mL) was added 3-bromobenzoyl chloride (2.9 mL, 22 mmol) and the reaction mixture was stirred at room temperature under nitrogen for 16 hours. The reaction mixture was then washed with 1 M hydrochloric acid (5×200 mL), 1 M sodium hydroxide (200 mL), and brine (200 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a yellow solid (7.2 g). Recrystallization from ethyl acetate gave the title compound (5.8 g, 72%) as a white crystalline solid.

Workup

  1. washThe reaction mixture was then washed with 1 M hydrochloric acid (5×200 mL), 1 M sodium hydroxide (200 mL), and brine (200 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18eb47bca0884e47bff8fbbe6273a173
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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