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

HRID 1845274ノート

反応式

HRID 1845274 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
135 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-aa29cf66c90046748c230dcea12b069a
出典データセット
uspto-grants-2015_02
特許番号
US08946439B2

反応ノート

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