Pivaloyl chloride → N-(5-Fluoropyridin-3-yl)-2,2-dimethylpropanamide

HRID 629731Notes

Reaction equation

HRID 629731 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[NH2:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([F:15])[CH:14]=1>ClCCl>[F:15][C:13]1[CH:14]=[C:9]([NH:8][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[CH:10]=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 5744505-Fluoro-3-pyridinamine

Product 1

HCID 86726332N-(5-Fluoropyridin-3-yl)-2,2-dimethylpropanamideYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pivaloyl chloride (18.8 mL, 153 mmol) was added to a solution of 3-amino-5-fluoropyridine (13.2 g, 118 mmol) and TEA (49.2 mL, 353 mmol) in Dichloromethane (235 mL) at 0° C. The reaction was warmed to ambient temperature and stirred for 1 hour. The reaction was quenched with saturated aqueous NaHCO3 and the mixture was extracted with dichloromethane (×3). The combined organic fractions were dried (MgSO4), filtered and the solvent was evaporated under reduced pressure to afford the title compound (22.5 g, 115 mmol, 97% yield) as a light brown solid, MS (ESI): m/z=197.35 (MH+), 100% pure by LCMS.

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3
  2. extractionthe mixture was extracted with dichloromethane (×3)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-81d49703a2ee42da895a47006fdaaf45
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

Loading…