Bromazepam → 8-Bromo-6-(2-pyridyl)-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid, ethyl ester

HRID 1111631Notes

Reaction equation

HRID 1111631 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=O)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[CH:19]=1.CC(C)([O-])C.[K+].P(Cl)(OCC)(OCC)=O.[N+:35]([CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])#[C-:36]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:36]=[N:35][C:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[C:10]3[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[CH:19]=1

Participants

6

Reactant 4

HCID 2441BromazepamHCID 13139Diethyl chlorophosphateHCID 533707Ethyl isocyanoacetateHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 210652848-Bromo-6-(2-pyridyl)-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 15.8 g (0.05 mol) of 7-bromo-1,3-dihydro-5-(2-pyridyl)-2H-1,4-benzodiazepin-2-one in 300 ml of dry tetrahydrofuran was cooled to 10° with stirring under argon. Potassium tert. butoxide 6.3 g (0.056 mol) was added and stirring was continued for 10 min. Following the addition of 14 ml of diethyl chlorophosphate the mixture was stirred for additional 20 min. A previously prepared mixture of 11.3 g ethyl isocyanoacetate, 11.3 g of potassium tert. butoxide and 300 ml of tetrahydrofuran was then poured into the reaction mixture.

Workup

  1. stirringstirring
  2. stirringwas stirred for additional 20 min
  3. additionwas then poured into the reaction mixture

Sources & evidence

ORD record
ord-4775d6204a8742ec833aafe76a94dd17
Source dataset
uspto-grants-1978_10
Patent number
US04118386

Reaction notes

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