N-bromobutanimide → tert-butyl 1-bromo-3-(trifluoromethyl)-5H,6H,7H,8H-imidazo(1,5-a)pyrazine-7-carboxylate

HRID 221477Notes

Reaction equation

HRID 221477 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([C:17]([F:20])([F:19])[F:18])=[N:15][CH:16]=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:21]N1C(=O)CCC1=O>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([C:17]([F:20])([F:18])[F:19])=[N:15][C:16]([Br:21])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57518450Imidazo[1,5-a]pyrazine-7(8h)-carboxylic acid,5,6-dihydro-3-(trifluoromethyl)-,1,1-dimethylethyl ester

Product 1

HCID 57518451tert-butyl 1-bromo-3-(trifluoromethyl)-5H,6H,7H,8H-imidazo(1,5-a)pyrazine-7-carboxylateYield 57.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 100 mL dried flask, the compound obtained from the previous step, 3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester 27a (300 mg, 1.04 mmol) was dissolved in 50 mL of ethanol under stirring, and N-bromosuccinimide (369 mg, 2.08 mmol) was then added to the solution. The reaction mixture was stirred at room temperature for an hour until the reaction was complete. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 1-bromo-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester 27b (220 mg, yield 57.8%) as a white solid.

Workup

  1. customIn a 100 mL dried flask
  2. stirringThe reaction mixture was stirred at room temperature for an hour until the reaction
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-53d29bf16ba34f61aba1c4953bfdb5d9
Source dataset
uspto-grants-2012_06
Patent number
US08207161B2

Reaction notes

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