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

HRID 1845285노트

반응식

HRID 1845285 반응식
[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]

참가 물질

7

반응물 2

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

생성물 1

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

시약·촉매·용매 4

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 1140Toluene용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-87a7dd84bd19447c9e3e78f5415f280d
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

반응 노트

불러오는 중…