Dimethyl Sulfoxide → Methyl 3-(5-methylpyridin-2-yl)-5-(thiazol-2-yloxy)benzoate

HRID 1845286노트

반응식

HRID 1845286 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Br[C:20]1[S:21][CH:22]=[CH:23][N:24]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>CCOC(C)=O>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:9]=[C:4]([CH:3]=[C:2]([O:1][C:20]3[S:21][CH:22]=[CH:23][N:24]=3)[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[N:13][CH:14]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 58188160Methyl 3-hydroxy-5-(5-methylpyridin-2-yl)benzoate

생성물 1

HCID 58188068Methyl 3-(5-methylpyridin-2-yl)-5-(thiazol-2-yloxy)benzoate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
135 °C

실험 절차

A stirred mixture of methyl 3-hydroxy-5-(5-methylpyridin-2-yl)benzoate (290 mg, 1.2 mmol), 2-bromothiazole (410 mg, 2.5 mmol), potassium carbonate (346 mg, 2.5 mmol), and dimethyl sulfoxide (5 mL) was heated at 135° C. overnight. The reaction mixture was then cooled to room temperature and diluted with EtOAc. The organic phase was washed with aq. NaHCO3 (sat.), dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (0-30% EtOAc/hexane) to afford the title compound.

후처리

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. washThe organic phase was washed with aq. NaHCO3 (sat.)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (0-30% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-d700671e81e34b619b4d8adaff40496d
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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