Methyl bromoacetate → HCID 59547971, compound

HRID 1946380Notes

Reaction equation

[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=2[C:20]([F:23])([F:22])[F:21])[N:8]=1)=[O:5].CC(C)([O-])C.[K+].Br[CH2:36][C:37]([O:39][CH3:40])=[O:38]>CS(C)=O>[F:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:2]([F:1])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[CH:15][C:14]=2[C:20]([F:23])([F:21])[F:22])[N:8]=1)=[O:5]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2,6-difluoro-N-(1-{[4-hydroxy-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)benzamide (for a preparation see Example 36)(81 mg, 0.204 mmol) in DMSO (0.5 ml) was added potassium t-butoxide (23 mg, 0.205 mmol). The reaction was stirred for 15 min before adding methyl bromoacetate (0.020 ml, 0.211 mmol, Aldrich). The reaction was heated to 60° C. and stirred overnight, under nitrogen. The reaction mixture was filtered through a hydrophobic frit and the filtrate diluted with methanol (0.5 ml) and the sample purified by MDAP on Sunfire C18 column using Acetonitrile-Water with a Formic acid modifier (Method B). The solvent was evaporated in vacuo to give the title compound as a brown gum (38.5 mg); LCMS: (System 4) MH+=470, tRET=2.90 min.

Workup

stirringstirred overnight, under nitrogen
filtrationThe reaction mixture was filtered through a hydrophobic frit
additionthe filtrate diluted with methanol (0.5 ml)
customthe sample purified by MDAP on Sunfire C18 column
customThe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-e06f73011e6c4257a5df835a79338765
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399436B2

Reaction notes

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