Tetrahydrofuran → 2-(Pyridin-4-yl)-5-(trifluoromethylthio)benzoxazole

HRID 2190763노트

반응식

HRID 2190763 반응식
O[C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[NH:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[N:18]1[CH:17]=[CH:16][C:15]([C:14]2[O:21][C:2]3[CH:7]=[CH:6][C:5]([S:8][C:9]([F:10])([F:11])[F:12])=[CH:4][C:3]=3[N:13]=2)=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 11776Triphenylphosphine2회HCID 220568ethyl N-ethoxycarbonyliminocarbamate2회HCID 66880242HCID 66880242, 화합물

생성물 1

HCID 668807602-(Pyridin-4-yl)-5-(trifluoromethylthio)benzoxazole수율 26.1%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

To a mixture of 0.69 g of N-[2-hydroxy-5-(trifluoromethylthio)phenyl]isonicotinamide, 9 ml of tetrahydrofuran, and 0.63 g of triphenylphosphine, 1.05 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature and stirred for three hours. To the mixture, 0.21 g of triphenylphosphine and 0.35 g of 40% toluene solution of diethyl azodicarboxylate were added. The reaction mixture was stirred for further two hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and the resultant crystals were washed with methanol to give 0.17 g of 2-(pyridin-4-yl)-5-(trifluoromethylthio)benzoxazole (hereinafter, referred to as “active compound 76”).

후처리

  1. additionwas added dropwise at room temperature
  2. stirringThe reaction mixture was stirred for further two hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washthe resultant crystals were washed with methanol

출처 및 근거

ORD 기록
ord-70ed7d9b47e044399fb3fa97766ff1e3
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324387B2

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