Potassium Carbonate → (4-Bromo-2-methyl-phenyl)-(5,11-dihydro-pyrido[2,3-b][1,5]benzodiazepin-6-yl)-methanone

HRID 378895

Reaction equation

HRID 378895 reaction equation
[N:1]1[C:6]2[NH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[NH:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[Br:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[C:25]([CH3:32])[CH:24]=1>CN(C)C=O.C(N(CC)C=O)C>[Br:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([N:10]2[C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[NH:7][C:6]3[N:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH2:11]2)=[O:28])=[C:25]([CH3:32])[CH:24]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 110307606,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepineHCID 128464834-Bromo-2-methylbenzoyl chloride

Product 1

HCID 15547049(4-Bromo-2-methyl-phenyl)-(5,11-dihydro-pyrido[2,3-b][1,5]benzodiazepin-6-yl)-methanoneYield 53.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 12051DiethylformamideSolvent

Procedure

To a solution of 6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (3 g, 15.2 mmol) in N,N-dimethylformamide under nitrogen was added solid potassium carbonate (6.3 g, 45.6 mmol). A solution of the crude 4-bromo-2-methylbenzoyl chloride (22.8 mmol) in N,N-diethylformamide was added dropwise, and the mixture stirred at room temperature for 15 minutes. Excess potassium carbonate was filtered off, the filtrate was washed with water and the aqueous layer was extracted with chloroform. The extracts were dried over anhydrous sodium sulfate, evaporated to dryness and the residue dissolved in dichloromethane and absorbed onto a silica Merck-60 flash column. Elution with 20% ethyl acetate in hexane provided the title compound (3.2 g) as a foam which crystallized upon sonication from ethanol hexane.

Workup

  1. filtrationExcess potassium carbonate was filtered off
  2. washthe filtrate was washed with water
  3. extractionthe aqueous layer was extracted with chloroform
  4. dry with materialThe extracts were dried over anhydrous sodium sulfate
  5. customevaporated to dryness
  6. dissolutionthe residue dissolved in dichloromethane
  7. customabsorbed onto a silica Merck-60 flash column
  8. washElution with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-15891177812a46ce937adeb4342eb50b
Source dataset
uspto-grants-2001_10
Patent number
US06297234B1

Linked notes

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