Bromomethylcyclopropane → HCID 59547832, compound

HRID 1946414Notes

Reaction equation

HRID 1946414 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]=[C:17]([OH:19])[CH:16]=[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][CH:37]1[CH2:39][CH2:38]1>CS(C)=O.CO>[CH:37]1([CH2:36][O:19][C:17]2[CH:16]=[CH:15][C:14]([C:20]([F:23])([F:21])[F:22])=[C:13]([CH2:12][N:9]3[CH:10]=[CH:11][C:7]([NH:6][C:4](=[O:5])[C:3]4[C:2]([F:1])=[CH:27][CH:26]=[CH:25][C:24]=4[F:28])=[N:8]3)[CH:18]=2)[CH2:39][CH2:38]1

Participants

6

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 23665647Potassium tert-butoxideHCID 59547881HCID 59547881, compound

Product 1

HCID 59547832HCID 59547832, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

To a solution of 2,6-difluoro-N-(1-{[5-hydroxy-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)benzamide (for a preparation see Intermediate 42)(75 mg, 0.189 mmol) in DMSO (1 ml) was added potassium t-butoxide (23 mg, 0.205 mmol, Aldrich). The solution was stirred at ambient temperature for 5 min. To the solution was added (bromomethyl)cyclopropane (0.023 ml, 0.245 mmol, Alfa Aesar) and the mixture stirred overnight at ambient temperature under nitrogen. The solution was diluted with methanol (1 ml) and purified by MDAP on Sunfire C18 column (Method B) using Acetonitrile-Water with a Formic acid modifier. The solvent was evaporated in vacuo to give the title compound as a white solid (36 mg); LCMS: (System 4) MH+=452, tRET=3.18 min.

Workup

  1. stirringthe mixture stirred overnight at ambient temperature under nitrogen
  2. custompurified by MDAP on Sunfire C18 column (Method B)
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-dacd389ab6ed4d2397edd04bbf501f2e
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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