Boron tribromide → HCID 59548014, compound

HRID 1946426Notes

Reaction equation

HRID 1946426 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([NH:10][C:11]1[CH:15]=[CH:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][C:18]=2[C:25]([F:28])([F:27])[F:26])[N:12]=1)=[O:9].B(Br)(Br)Br>ClCCl>[OH:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:13]2[CH:14]=[CH:15][C:11]([NH:10][C:8]([C:7]3[CH:6]=[CH:5][N:4]=[CH:3][C:2]=3[CH3:1])=[O:9])=[N:12]2)=[C:18]([C:25]([F:27])([F:28])[F:26])[CH:19]=1

Participants

4

Reactant 2

HCID 25134Boron tribromide3×HCID 59547925HCID 59547925, compound

Product 1

HCID 59548014HCID 59548014, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent5×

Procedure

To a solution of 3-methyl-N-(1-{[4-(methyloxy)-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-4-pyridinecarboxamide (for a preparation see Example 175)(50 mg, 0.128 mmol) in dichloromethane (1 mL) was added slowly 1.0 M boron tribromide in DCM (0.26 mL, 0.260 mmol). The resulting colourless solution was stirred under nitrogen for 2 days. The reaction mixture ran dry, so further amounts of dichloromethane (1 ml) and 1.0 M boron tribromide in DCM (0.26 mL, 0.260 mmol) were added. The resulting white suspension was stirred at ambient temperature under nitrogen overnight. A further amount of 1.0 M boron tribromide in DCM (0.26 ml, 0.26 mmol) was added and stirred for a further 4 h. The solvent was removed in vacuo and the residue dissolved in 1:1 MeOH:DMSO (1 ml) and purified by MDAP on an Xbridge column using Acetonitrile-Water with an ammonium carbonate modifier (Method E). The solvent was evaporated in vacuo to give the title compound as a white solid (11 mg); LCMS (System 8) MH+=376, tRET=2.13 min.

Workup

  1. customThe reaction mixture ran dry
  2. stirringThe resulting white suspension was stirred at ambient temperature under nitrogen overnight
  3. stirringstirred for a further 4 h
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue dissolved in 1:1 MeOH
  6. customDMSO (1 ml) and purified by MDAP on an Xbridge column
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-739eaa64540c445a8f1a8374ac84042b
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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