Butyl bromide → N-(1-{[4-(Butyloxy)-2-chlorophenyl]methyl}-1H-pyrazol-3-yl)-2,6-difluorobenzamide

HRID 1946374Notes

Reaction equation

HRID 1946374 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:9]=1[CH2:15][N:16]1[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:31])[C:23]2[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=2[F:30])=[N:17]1.Br[CH2:33][CH2:34][CH2:35][CH3:36]>CS(C)=O.CO>[CH2:33]([O:14][C:12]1[CH:11]=[CH:10][C:9]([CH2:15][N:16]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:31])[C:23]3[C:24]([F:30])=[CH:25][CH:26]=[CH:27][C:28]=3[F:29])=[N:17]2)=[C:8]([Cl:7])[CH:13]=1)[CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 23665647Potassium tert-butoxideHCID 59547950N-{1-[(2-Chloro-4-hydroxyphenyl)methyl]-1H-pyrazol-3-yl}-2,6-difluorobenzamide

Product 1

HCID 59547973N-(1-{[4-(Butyloxy)-2-chlorophenyl]methyl}-1H-pyrazol-3-yl)-2,6-difluorobenzamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

Potassium t-butoxide (9.7 mg, 0.086 mmol, Aldrich) was added to a solution of N-{1-[(2-chloro-4-hydroxyphenyl)methyl]-1H-pyrazol-3-yl}-2,6-difluorobenzamide (for a preparation see Example 31)(29.4 mg, 0.081 mmol) in DMSO (0.5 ml). The reaction was stirred for 5 min before adding 1-bromobutane (10.42 μL, 0.097 mmo, Acros). The reaction was stirred for 56 h at ambient temperature. The reaction mixture was 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 yellow gum (14.5 mg); LCMS: (System 4) MH+=420, tRET=3.45 min.

Workup

  1. stirringThe reaction was stirred for 56 h at ambient temperature
  2. customthe sample purified by MDAP on Sunfire C18 column
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-d575ab9fd5984495bd81668c79484bca
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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