Boron tribromide → HCID 58541878, compound

HRID 1966682Notes

Reaction equation

HRID 1966682 reaction equation
[C:1]([N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[CH:15]=[N:16][C:17]([NH2:20])=[N:18][CH:19]=3)=[CH:13][C:8]=2[N:7]=[C:6]1[C:21]1[CH:26]=[C:25]([O:27]C)[CH:24]=[CH:23][C:22]=1[N:29]1[CH:33]=[CH:32][CH:31]=[N:30]1)([CH3:4])([CH3:3])[CH3:2].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:20][C:17]1[N:18]=[CH:19][C:14]([C:12]2[CH:11]=[CH:10][C:9]3[N:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:6]([C:21]4[CH:26]=[C:25]([OH:27])[CH:24]=[CH:23][C:22]=4[N:29]4[CH:33]=[CH:32][CH:31]=[N:30]4)=[N:7][C:8]=3[CH:13]=2)=[CH:15][N:16]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 585419375-[1-tert-Butyl-2-(5-methoxy-2-pyrazol-1-yl-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine

Product 1

HCID 58541878HCID 58541878, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[1-tert-butyl-2-(5-methoxy-2-pyrazol-1-yl-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine (Example 2) (75 mg, 0.17 mmol) in CH2Cl2 (10 mL) is added BBr3 (1M in THF) (0.5 mL, 0.51 mmol) at 0° C. under nitrogen atmosphere. The solution is warmed to room temperature and stirred for 48 hours. The solution is cooled down to 4° C. and saturated NaHCO3 solution (5 mL) is added. The mixture is extracted with EtOAc (3×10 mL) and the combined organic layer is dried (MgSO4), filtered and concentrated and the residue is purified by silica gel flash chromatography eluting with 10% MeOH in CH2Cl2 to afford the title compound (10 mg, 14%) as a white foam. LCMS (ESMS): m/z 426.20 (M++1)

Workup

  1. temperatureThe solution is cooled down to 4° C.
  2. extractionThe mixture is extracted with EtOAc (3×10 mL)
  3. dry with materialthe combined organic layer is dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue is purified by silica gel flash chromatography
  7. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-ec4ead4876e64fd3bd507beb12b332df
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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