Formic Acid → N-(6-bromo-2-methoxypyridin-3-yl)formamide

HRID 475718Notes

Reaction equation

HRID 475718 reaction equation
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[Br:11][C:12]1[N:17]=[C:16]([O:18][CH3:19])[C:15]([NH2:20])=[CH:14][CH:13]=1>C1COCC1>[Br:11][C:12]1[N:17]=[C:16]([O:18][CH3:19])[C:15]([NH:20][CH:8]=[O:10])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 105361376-Bromo-2-methoxypyridin-3-amine

Product 1

HCID 71492501N-(6-bromo-2-methoxypyridin-3-yl)formamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of acetic anhydride (8.54 mL, 24.63 mmol) and formic acid (12.8 mL, 24.63 mmol) was stirred at room temperature for 40 min. To this mixture 6-bromo-2-methoxypyridin-3-amine (5.000 g, 24.63 mmol) in 30 mL of THF was added dropwise. The resulting solution was heated at 60° C. with stirring for 16 h. Upon cooling, the reaction mixture was poured into icewater. The resulting precipitate was filtered to give N-(6-bromo-2-methoxypyridin-3-yl)formamide (5.690 g, 24.63 mmol, 100% yield) as light brown solid. LC-MS (M+Na)+=231.0.

Workup

  1. temperatureThe resulting solution was heated at 60° C.
  2. stirringwith stirring for 16 h
  3. temperatureUpon cooling
  4. additionthe reaction mixture was poured into icewater
  5. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-6bae5e2d3e7b44ab8d1a5b80af043a77
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

Loading…