Acetone → (4-{[4-Difluoromethoxy-2-ethyl-8-fluoro-5-(2-methoxy-2-oxoethoxy) quinolin-3-yl]methyl}phenyl)boronic acid

HRID 1922125노트

반응식

HRID 1922125 반응식
[CH3:1][O:2][C:3](=[O:39])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:35][CH:36]([F:38])[F:37])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([B:26]3[O:30]C(C)(C)C(C)(C)[O:27]3)=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.I([O-])(=O)(=O)=O.[Na+].C([O-])(=O)C.[NH4+].CC(C)=O>O>[F:38][CH:36]([F:37])[O:35][C:8]1[C:7]2[C:12](=[C:13]([F:16])[CH:14]=[CH:15][C:6]=2[O:5][CH2:4][C:3]([O:2][CH3:1])=[O:39])[N:11]=[C:10]([CH2:17][CH3:18])[C:9]=1[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([B:26]([OH:30])[OH:27])=[CH:24][CH:25]=1

참가 물질

6

반응물 4

HCID 180AcetoneHCID 517165Ammonium AcetateHCID 23667635Sodium periodateHCID 67458783{4-Difluoromethoxy-2-ethyl-8-fluoro-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzyl]quinolin-5-yloxy}acetic acid methyl ester

생성물 1

HCID 67458287(4-{[4-Difluoromethoxy-2-ethyl-8-fluoro-5-(2-methoxy-2-oxoethoxy) quinolin-3-yl]methyl}phenyl)boronic acid수율 92.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of {4-difluoromethoxy-2-ethyl-8-fluoro-3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]quinolin-5-yloxy}acetic acid methyl ester (0.89 g), sodium periodate (1.7 g), ammonium acetate (0.46 g), acetone (23 mL) and water (11 mL) was stirred at room temperature for 41 hours. The mixture was concentrated to low bulk under reduced pressure, and the residue was diluted with water and then extracted with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and then concentrated under reduced pressure to afford title compound (0.70 g).

후처리

  1. concentrationThe mixture was concentrated to low bulk under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-aaf341536a954aecabf132d64a03d1b1
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173812B2

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