Ammonium → 3-(2-Fluorobenzyl)imidazo[1,5-a]pyridine-1-carboxamide

HRID 1875449Notes

Reaction equation

HRID 1875449 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][C:5]1[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([C:14](OCC)=[O:15])[N:6]=1.[NH4+:23].CO>O>[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][C:5]1[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([C:14]([NH2:23])=[O:15])[N:6]=1

Participants

5

Reactant 3

HCID 223AmmoniumHCID 887MethanolHCID 59177857Ethyl 3-(2-fluorobenzyl)imidazo[1,5-a]pyridine-1-carboxylate

Product 1

HCID 591778703-(2-Fluorobenzyl)imidazo[1,5-a]pyridine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

560 mg (1.88 mmol) of ethyl 3-(2-fluorobenzyl)imidazo[1,5-a]pyridine-1-carboxylate from example 7A are heated in 55 ml of 33% strength aqueous ammonium solution in a microwave at 130° C. for 3 h. The mixture is diluted with water, and, after addition of some methanol, extracted with ethyl acetate. The organic phase is dried over sodium sulfate and concentrated. 229 mg (87.5% purity, 40% of theory) of the desired compound are obtained as greenish crystals which are reacted without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-86fef6edfb0f44dcb6b9b9e3cb2bffa9
Source dataset
uspto-grants-2012_11
Patent number
US08309551B2

Reaction notes

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