5-Methyl-2-(tri-n-butylstannyl)pyridine → Methyl 3-hydroxy-5-(5-methylpyridin-2-yl)benzoate

HRID 1845285ノート

反応式

HRID 1845285 の反応式
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6](Br)[CH:5]=1.[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([Sn](CCCC)(CCCC)CCCC)=[N:18][CH:19]=1>C1(C)C=CC=CC=1.CN(C=O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:10][C:8]1[CH:9]=[C:4]([CH:5]=[C:6]([C:17]2[CH:16]=[CH:15][C:14]([CH3:13])=[CH:19][N:18]=2)[CH:7]=1)[C:3]([O:2][CH3:1])=[O:12]

参加物

7

反応物 2

HCID 111327115-Methyl-2-(tri-n-butylstannyl)pyridineHCID 53216607Methyl 3-bromo-5-hydroxybenzoate

生成物 1

HCID 58188160Methyl 3-hydroxy-5-(5-methylpyridin-2-yl)benzoate

試薬・触媒・溶媒 4

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3-bromo-5-hydroxy-benzoic acid methyl ester (1.47 g, 6.36 mmol), 5-methyl-2-(tributylstannyl)pyridine (3.0 g, 7.85 mmol), tetrakis(triphenylphosphine)-palladium(0) (300 mg, 0.26 mmol) in toluene (20 mL) and DMF (2 mL) was subjected to microwave irradiation at 110° C. for 1 hour. After cooling, the mixture was diluted with water and extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography to afford the title compound as a white solid.

後処理

  1. customirradiation at 110° C. for 1 hour
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-87a7dd84bd19447c9e3e78f5415f280d
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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