Methanol → HCID 59507321, 화합물

HRID 2096801노트

반응식

HRID 2096801 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 59507321HCID 59507321, 화합물수율 89.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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+].

후처리

  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)

출처 및 근거

ORD 기록
ord-0a15ae2421a74802b0c01aa4fb388b6a
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450313B2

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