Phosphorus tribromide → HCID 59547848, compound

HRID 1946312Notes

Reaction equation

HRID 1946312 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[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]([CH2:19]O)=[CH:15][C:14]=2[C:21]([F:24])([F:23])[F:22])[N:8]=1)=[O:5].P(Br)(Br)[Br:31]>C(Cl)Cl.C(=O)([O-])O.[Na+]>[Br:31][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:9]2[CH:10]=[CH:11][C:7]([NH:6][C:4](=[O:5])[C:3]3[C:2]([F:1])=[CH:28][CH:27]=[CH:26][C:25]=3[F:29])=[N:8]2)=[C:14]([C:21]([F:24])([F:23])[F:22])[CH:15]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 59547991HCID 59547991, compound

Product 1

HCID 59547848HCID 59547848, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 2,6-difluoro-N-(1-{[4-(hydroxymethyl)-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)benzamide (for a preparation see Example 44) (0.119 g, 0.289 mmol) in DCM (6.5 ml) in an ice-water bath under nitrogen was added phosphorus tribromide (0.027 ml, 0.289 mmol, Aldrich). The cloudy mixture was allowed to warm to ambient temperature and stirred for 1 h. The reaction mixture was diluted with saturated sodium hydrogen carbonate aqueous (15 ml) and ice (15 ml). The biphasic mixture was diluted with DCM (25 ml). The phases were separated and the aqueous phase washed with DCM (20 ml). The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound a colourless gum (98 mg). LCMS: (System 4) MH+=475.9, tRET=3.06 min.

Workup

  1. customThe phases were separated
  2. washthe aqueous phase washed with DCM (20 ml)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-33a2854cd6a04b28b13ee27343a1c3e3
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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