Bromomethylcyclopropane → HCID 59547975, compound

HRID 1946359Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH2:9][N:10]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])=[N:11]1.[CH3:26][C:27]([CH3:30])([O-])[CH3:28].[K+].BrCC1CC1>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:26][CH:27]2[CH2:30][CH2:28]2)=[CH:4][C:3]=1[CH2:9][N:10]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[C:17]2[C:18]([F:24])=[CH:19][CH:20]=[CH:21][C:22]=2[F:23])=[N:11]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-{1-[(2-chloro-5-hydroxyphenyl)methyl]-1H-pyrazol-3-yl}-2,6-difluorobenzamide (for as preparation see Intermediate 13) (46 mg, 0.126 mmol) in DMSO (0.5 ml) was added potassium t-butoxide (15 mg, 0.134 mmol). The reaction was stirred for 10 min. To the reaction mixture was added (bromomethyl)cyclopropane (0.012 ml, 0.126 mmol, Lancaster). 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 white solid (15.6 mg); LCMS: (System 4) MH+=418, tRET=3.20 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-fbcf9c61aea94953accffaa082de9419
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399436B2

Reaction notes

Loading…