Water → 3-(2-Fluorobenzyl)imidazo[1,5-a]pyridine-1-carbonitrile

HRID 1875450Notes

Reaction equation

HRID 1875450 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][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]([NH2:16])=O)[N:6]=1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>C1COCC1>[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][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]#[N:16])[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 591778703-(2-Fluorobenzyl)imidazo[1,5-a]pyridine-1-carboxamide

Product 1

HCID 591778713-(2-Fluorobenzyl)imidazo[1,5-a]pyridine-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

269 mg (1.00 mmol) of 3-(2-fluorobenzyl)imidazo[1,5-a]pyridine-1-carboxamide from example 17A are dissolved in 2.5 ml of THF, and 200 mg (2.50 mmol) of pyridine and 525 mg (2.50 mmol) of trifluoroacetic anhydride are added. The mixture is stirred at RT for 15 h, then water is added, and the mixture is extracted with ethyl acetate. The organic phase is washed with saturated sodium bicarbonate solution and 1 N hydrochloric acid, dried over sodium sulfate and concentrated. The crude product obtained (188 mg, 61% purity, 45% of theory) is reacted without further purification.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic phase is washed with saturated sodium bicarbonate solution and 1 N hydrochloric acid
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bf8f65cb7168496785883b6bc2abade3
Source dataset
uspto-grants-2012_11
Patent number
US08309551B2

Reaction notes

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