Sodium Bicarbonate → Ethyl imidazo[1,5-a]pyridine-8-carboxylate

HRID 1471705Notes

Reaction equation

HRID 1471705 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1.[C:15]([O-])(O)=O.[Na+]>>[CH:3]1[N:2]=[CH:15][N:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4]=12

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 86280247Ethyl 2-(aminomethyl)nicotinate hydrochloride

Product 1

HCID 69160068Ethyl imidazo[1,5-a]pyridine-8-carboxylate

Procedure

A mixture of 44.8 mL of acetic anhydride and 19.2 mL of formic acid was heated in a 50-60° C. oil bath temperature for 3 h and then cooled to rt to give formic-acetic anhydride, which was then slowly added to the solid ethyl 2-(aminomethyl)-3-pyridinecarboxylate HCl and then stirred at rt for 8 h. Excess reagent was evaporated to give a residue, which was neutralized by very slow addition of sat. NaHCO3 solution. Solution was extracted with DCM, dried and evaporated to provide ethyl imidazo[1,5-a]pyridine-8-carboxylate as a yellow solid (crude weight 2.7 g). MS: exact mass calculated for C10H10N2O2, 190.07; m/z found, 191 [M+H]+.

Workup

  1. customExcess reagent was evaporated
  2. customto give a residue, which
  3. extractionSolution was extracted with DCM
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-8ffeb8ec436f42f08706c2a3f0e91603
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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