Dichloromethane → Ethyl 3-(5-(2-(bromomethyl)-4,5-difluorophenyl)picolinamido)propanoate

HRID 405207Notes

Reaction equation

HRID 405207 reaction equation
[C:1]([Br:5])(Br)(Br)Br.C(Cl)Cl.[F:9][C:10]1[C:15]([F:16])=[CH:14][C:13]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([NH:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:24])=[N:21][CH:22]=2)=[C:12](CO)[CH:11]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(OCC)C>[Br:5][CH2:1][C:12]1[CH:11]=[C:10]([F:9])[C:15]([F:16])=[CH:14][C:13]=1[C:17]1[CH:18]=[CH:19][C:20]([C:23]([NH:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:24])=[N:21][CH:22]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 71060054Ethyl 3-(5-(4,5-difluoro-2-(hydroxymethyl)phenyl)picolinamido)propanoate

Product 1

HCID 86674272Ethyl 3-(5-(2-(bromomethyl)-4,5-difluorophenyl)picolinamido)propanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Neat CBr4 (4.6 g, 13.7 mmol) was added to a 0° C., DCM solution (66 mL) of ethyl 3-(5-(4,5-difluoro-2-(hydroxymethyl)phenyl)picolinamido)propanoate (4.2 g, 11.4 mmol) and PPh3 (3.6 g, 13.7 mmol), the cold bath was removed, and the resulting mixture was allowed to warm to room temperature. After 2 h the resulting mixture was diluted with diethyl ether, filtered through a pad of CELITE, concentrated and purified via column chromatography to yield the title compound.

Workup

  1. filtrationfiltered through a pad of CELITE
  2. concentrationconcentrated
  3. custompurified via column chromatography

Sources & evidence

ORD record
ord-f6d217512ffa420587911d918a118dc3
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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