Potassium Carbonate → Ethyl 3-(5-(2-(((3-chloro-4-iodophenyl)amino)methyl)-4,5-difluorophenyl)picolinamido)propanoate

HRID 405208Notes

Reaction equation

HRID 405208 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([F:9])[C:6]([F:10])=[CH:5][C:4]=1[C:11]1[CH:12]=[CH:13][C:14]([C:17]([NH:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:18])=[N:15][CH:16]=1.[Cl:27][C:28]1[CH:29]=[C:30]([CH:32]=[CH:33][C:34]=1[I:35])[NH2:31].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:27][C:28]1[CH:29]=[C:30]([NH:31][CH2:2][C:3]2[CH:8]=[C:7]([F:9])[C:6]([F:10])=[CH:5][C:4]=2[C:11]2[CH:12]=[CH:13][C:14]([C:17]([NH:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:18])=[N:15][CH:16]=2)[CH:32]=[CH:33][C:34]=1[I:35]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2829263-Chloro-4-iodoanilineHCID 86674272Ethyl 3-(5-(2-(bromomethyl)-4,5-difluorophenyl)picolinamido)propanoate

Product 1

HCID 71060063Ethyl 3-(5-(2-(((3-chloro-4-iodophenyl)amino)methyl)-4,5-difluorophenyl)picolinamido)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 3-(5-(2-(bromomethyl)-4,5-difluorophenyl)picolinamido)propanoate (1.0 g, 2.3 mmol), 3-chloro-4-iodoaniline (1.2 g, 4.7 mmol), and K2CO3 (647 mg, 4.7 mmol) were diluted with DMF (2.4 mL) and the resulting mixture was stirred at room temperature. After 2 h the resulting mixture directly purified via column chromatography to yield the title compound.

Workup

  1. customAfter 2 h the resulting mixture directly purified via column chromatography

Sources & evidence

ORD record
ord-8a51dfdab8e5493ebad253b56c4b69cd
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

Loading…