Phosphorus oxychloride → Ethyl 3-(2-fluorobenzyl)imidazo[1,5-a]pyridine-1-carboxylate

HRID 1875440Notes

Reaction equation

HRID 1875440 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH:5]([NH:12][C:13](=O)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[CH3:2].P(Cl)(Cl)(Cl)=O>ClCCCl>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][C:13]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:23])[N:12]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 59177860Ethyl{[(2-fluorophenyl)acetyl]amino}(pyridin-2-yl)acetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2.72 g (8.60 mmol) of ethyl {[(2-fluorophenyl)acetyl]amino}(pyridin-2-yl)acetate from example 6A are introduced into 30 ml of 1,2-dichloroethane, and 4.81 ml (51.6 mmol) of phosphoryl chloride are added. The mixture is heated to reflux for 9 h and then concentrated in vacuo, and the residue is taken up in ethyl acetate. The solution is washed with saturated sodium carbonate solution, dried over sodium sulfate and purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1). 2.16 g (84% of theory) of the desired compound are obtained as a dark oil.

Workup

  1. additionare added
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 9 h
  4. concentrationconcentrated in vacuo
  5. washThe solution is washed with saturated sodium carbonate solution
  6. dry with materialdried over sodium sulfate
  7. custompurified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-e216e43e8f5a4708809b8be91ea56c48
Source dataset
uspto-grants-2012_11
Patent number
US08309551B2

Reaction notes

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