Dimethyl Sulfoxide → Methyl 4'-methyl-5-(pyridin-2-yloxy)biphenyl-3-carboxylate

HRID 1845274노트

반응식

HRID 1845274 반응식
[OH:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.CS(C)=O>CCOC(C)=O>[CH3:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[CH:7]=[C:2]([O:1][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=2)=[CH:13][CH:12]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 58187967Methyl 5-hydroxy-4'-methyl-[1,1'-biphenyl]-3-carboxylate

생성물 1

HCID 58188387Methyl 4'-methyl-5-(pyridin-2-yloxy)biphenyl-3-carboxylate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
135 °C

실험 절차

A mixture of methyl 5-hydroxy-4′-methylbiphenyl-3-carboxylate (100 mg, 0.41 mmol), potassium carbonate (100 mg, 0.72 mmol), 2-bromopyridine (0.40 mL, 4.2 mmol), and dimethyl sulfoxide (2 mL) was stirred at 135° C. overnight. After cooling, the mixture was diluted with EtOAc and washed with aq. NaHCO3 (sat.), dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (0-20% EtOAc/hexane) to afford the title compound.

후처리

  1. temperatureAfter cooling
  2. washwashed with aq. NaHCO3 (sat.)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (0-20% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-aa29cf66c90046748c230dcea12b069a
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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