Triphenylphosphonium bromide → HCID 24755049, compound

HRID 268639

Reaction equation

[CH2:1]([NH:8][C:9]([C:11]1[C:15]([CH:16]([CH3:18])[CH3:17])=[C:14]([CH2:19]O)[N:13]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[N:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BrH:28].[C:29]1([P:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(#N)C>[Br-:28].[CH2:1]([NH:8][C:9]([C:11]1[C:15]([CH:16]([CH3:18])[CH3:17])=[C:14]([CH2:19][P+:35]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:13]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[N:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-(4-fluoro-phenyl)-5-hydroxymethyl-4-isopropyl-1H-pyrazole-3-carboxylic acid benzylamide (0.525 g, 1.43 mmol) in acetonitrile (50 mL) was added triphenylphosphine hydrobromide (0.49 g, 1.43 mmol; commercially available from Sigma Aldrich). The reaction was heated to 80° C. for 24 hr after which time all starting material was consumed as determined by TLC. The reaction solvent was removed under reduced pressure and the resulting white solid was dried under high vacuum for 12 hr to provide [5-benzylcarbamoyl-2-(4-fluoro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethyl]-triphenyl-phosphonium bromide (0.977 g, 98%) in sufficient purity for use in the next step.

Workup

customwas consumed
customThe reaction solvent was removed under reduced pressure
customthe resulting white solid was dried under high vacuum for 12 hr

Sources & evidence

ORD record: ord-4cf3b6a1e1594ce88e6d669c3eaa36b9
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446121B2

Linked notes

Loading…