Phosphorus oxychloride → 3-(5-Methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,5-a]pyridine

HRID 747858

반응식

HRID 747858 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9]([C:11]1[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:13][O:14][C:15]=1[CH3:16])=O.P(Cl)(Cl)(Cl)=O.C(=O)(O)[O-].[Na+]>ClC(Cl)C.ClCCl>[CH3:16][C:15]1[O:14][N:13]=[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]=1[C:9]1[N:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]2=[CH:7][N:8]=1

참가 물질

6

반응물 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 7008625-methyl-3-phenyl-N-(pyridin-2-ylmethyl)-1,2-oxazole-4-carboxamide

생성물 1

HCID 162148953-(5-Methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,5-a]pyridine수율 47.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid (pyridin-2-ylmethyl)-amide (0.293 g, 1 mmol) in dichloroethane (5 mL) was added phosphorus oxychloride (0.47 mL, 5 mmol) via a syringe and the resulting mixture heated under reflux overnight. After cooling to room temperature, the mixture was diluted with dichloromethane. Cold saturated sodium bicarbonate (15 mL) was then added slowly and the mixture was vigorously stirred for 15 min. The organic layer was separated and the aqueous was extracted with dichloromethane. The combined extracts were washed with water, dried over sodium sulphate, and evaporated. Purification by preparative HPLC on reversed phase [0.1% aq. ammonia (25%)] afforded the title compound (0.13 g, 47%) as an orange solid. MS: m/e: 276.1 [M+H]+.

후처리

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux overnight
  3. customThe organic layer was separated
  4. extractionthe aqueous was extracted with dichloromethane
  5. washThe combined extracts were washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customPurification by preparative HPLC on reversed phase [0.1% aq. ammonia (25%)]

출처 및 근거

ORD 기록
ord-4228684736b64a7aa6320801e1172ff2
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399769B2

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