Butyl bromide → HCID 59547836, compound

HRID 1946358Notes

Reaction equation

HRID 1946358 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.CC(C)([O-])C.[K+].Br[CH2:33][CH2:34][CH2:35][CH3:36]>CS(C)=O>[CH2:33]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH2:9][N:10]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[C:17]3[C:18]([F:24])=[CH:19][CH:20]=[CH:21][C:22]=3[F:23])=[N:11]2)[CH:4]=1)[CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 23665647Potassium tert-butoxideHCID 59547885HCID 59547885, compound2×

Product 1

HCID 59547836HCID 59547836, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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) (35 mg, 0.096 mmol) in DMSO (0.5 ml) was added potassium t-butoxide (10.80 mg, 0.096 mmol). The reaction was stirred for 5 min before adding 1-bromobutane (0.012 ml, 0.115 mmol, Acros). The reaction mixture was stirred under nitrogen for 72 h at ambient temperature. 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 (11.2 mg); LCMS: (System 4) MH+=420, tRET=3.41 min.

Workup

  1. stirringThe reaction mixture was stirred under nitrogen for 72 h at ambient temperature
  2. filtrationThe reaction mixture was filtered through a hydrophobic frit
  3. additionthe filtrate diluted with methanol (0.5 ml)
  4. customthe sample purified by MDAP on Sunfire C18 column
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-7fd6264158af42beb4f8b0910d400456
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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