Methanol → HCID 59507321、化合物

HRID 2096801ノート

反応式

HRID 2096801 の反応式
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]

参加物

6

反応物 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 67545821HCID 67545821、化合物

生成物 1

HCID 59507321HCID 59507321、化合物収率 89.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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+].

後処理

  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)

出典と根拠

ORDレコード
ord-0a15ae2421a74802b0c01aa4fb388b6a
出典データセット
uspto-grants-2013_05
特許番号
US08450313B2

反応ノート

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