Methanol → HCID 59507321, compound

HRID 2386790Notes

Reaction equation

HRID 2386790 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-0d7732b876cf4e839be5dfa782e1099e
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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