Carbon tetrabromide → Ethyl 3-(5-(2-(bromomethyl)-3-isopropyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405260Notes

Reaction equation

HRID 405260 reaction equation
[C:1]([Br:5])(Br)(Br)Br.OC[C:8]1[C:13]([CH:14]([CH3:16])[CH3:15])=[CH:12][C:11]([C:17]([F:20])([F:19])[F:18])=[CH:10][C:9]=1[C:21]1[CH:22]=[CH:23][C:24]([C:27]([NH:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:28])=[N:25][CH:26]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:5][CH2:1][C:8]1[C:13]([CH:14]([CH3:16])[CH3:15])=[CH:12][C:11]([C:17]([F:20])([F:18])[F:19])=[CH:10][C:9]=1[C:21]1[CH:22]=[CH:23][C:24]([C:27]([NH:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:28])=[N:25][CH:26]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 71059694Ethyl 3-(5-(2-(hydroxymethyl)-3-isopropyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Product 1

HCID 86674291Ethyl 3-(5-(2-(bromomethyl)-3-isopropyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Neat CBr4 (57 mg, 0.17 mmol) was added to a DCM solution (5 mL) of ethyl 3-(5-(2-(hydroxymethyl)-3-isopropyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate (75 mg, 0.17 mmol) and PPh3 (45 mg, 0.17 mmol) and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture was concentrated and purified via column chromatography to yield the title compound.

Workup

  1. concentrationAfter 16 h the resulting mixture was concentrated
  2. custompurified via column chromatography

Sources & evidence

ORD record
ord-2625bbba1df840c8816bc7ffe75e34e3
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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