Water → 2-Methyl-3-(5-methylisoxazol-4-yl)-6-methoxypyridine

HRID 900068노트

반응식

HRID 900068 반응식
I[C:2]1[CH:3]=[N:4][O:5][C:6]=1[CH3:7].[CH3:8][O:9][C:10]1[N:15]=[C:14]([CH3:16])[C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)(O)[O-].[Na+].O>COCCOC>[CH3:16][C:14]1[C:13]([C:2]2[CH:3]=[N:4][O:5][C:6]=2[CH3:7])=[CH:12][CH:11]=[C:10]([O:9][CH3:8])[N:15]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27630842-Methyl-6-methoxypyridine-3-boronic acidHCID 27954614-Iodo-5-methylisoxazole

생성물 1

HCID 210719302-Methyl-3-(5-methylisoxazol-4-yl)-6-methoxypyridine수율 40.2%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of 4-iodo-5-methylisoxazole (18.2 g, 87 mmol), 6-methoxy-2-methylpyridine-3-boronic acid (14.6 g, 87 mmol), sodium bicarbonate (22.0 g, 262 mmol), water (150 mL) and DME (150 mL) was degassed three times with stirring by the application of a vacuum and then introduction of a nitrogen atmosphere. [1,1-Bis(diphenylphosphino)ferrocene]-dichloropalladium (II) (2.14 g, 2.6 mmol) was added in one portion. The reaction mixture was degassed as before. The reaction mixture was then stirred at 80° C. for 4 h, then it was cooled to ambient temperature. Three extractions with EtOAc, drying the combined organic layers over MgSO4, filtration and removal of solvent in vacuo afforded an oil. Flash chromatography (EtOAc:hexane::1:9) and removal of solvent in vacuo from the desired fractions gave the product (7.15 g): 1H-NMR(CDCl3, 300 MHz): δ 8.16 (s, 1H), 7.33 (d, 1H, J=8), 6.63 (d, 1H, J=8), 3.95 (s, 3H), 2.35 (s, 6H); APCI+-MS: 205 (M++H).

후처리

  1. customwas degassed three times
  2. customThe reaction mixture was degassed as before
  3. stirringThe reaction mixture was then stirred at 80° C. for 4 h
  4. extractionThree extractions with EtOAc
  5. customdrying the combined organic layers
  6. filtrationover MgSO4, filtration and removal of solvent in vacuo
  7. customafforded an oil
  8. customFlash chromatography (EtOAc:hexane::1:9) and removal of solvent in vacuo from the desired fractions

출처 및 근거

ORD 기록
ord-47cc0fee7ab841b68a62620b8ca85689
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07358252B2

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