Methanol → HCID 59507321, compound

HRID 2096801Notes

Reaction equation

HRID 2096801 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:11]=[C:10]([O:12]C)[CH:9]=[CH:8][C:7]=1[CH:14]([CH3:33])[C:15]([C:21]1[CH:32]=[CH:31][C:24]2[N:25]([CH3:30])[C:26](=[O:29])[N:27]([CH3:28])[C:23]=2[CH:22]=1)([OH:20])[C:16]([F:19])([F:18])[F:17].CO.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:5][C:6]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:7]=1[CH:14]([CH3:33])[C:15]([C:21]1[CH:32]=[CH:31][C:24]2[N:25]([CH3:30])[C:26](=[O:29])[N:27]([CH3:28])[C:23]=2[CH:22]=1)([OH:20])[C:16]([F:17])([F:18])[F:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 67545821HCID 67545821, compound

Product 1

HCID 59507321HCID 59507321, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1M solution of boron tribromide in DCM (3.7 ml) was added to a solution of 5-[2-(2-chloro-4-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (300 mg) in DCM (10 ml). at −65° C. The mixture was allowed to warm to room temperature and then stirred for 4 h. MeOH (1.4 ml) and saturated aqueous NaHCO3 solution were added and stirred for 30 min. The mixture was extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated to an oil. The residue was purified by flash chromatography (SiO2, 30 to 100% EtOAc/heptane) to give the title compound (259 mg) as a light yellow oil. MS (m/e)=415.3 [M+H+].

Workup

  1. customat −65° C
  2. stirringstirred for 30 min
  3. extractionThe mixture was extracted with DCM
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated to an oil
  6. customThe residue was purified by flash chromatography (SiO2, 30 to 100% EtOAc/heptane)

Sources & evidence

ORD record
ord-0a15ae2421a74802b0c01aa4fb388b6a
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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