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

HRID 884833노트

반응식

HRID 884833 반응식
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:5]=[CH:6][C:7]([OH:19])=[C:8]([NH:10][C:11](=O)[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:9]=1.O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O.C1(C)C=CC=CC=1>[N:15]1[CH:16]=[CH:17][C:12]([C:11]2[O:19][C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:21])([F:20])[F:1])=[CH:9][C:8]=3[N:10]=2)=[CH:13][CH:14]=1

참가 물질

7

반응물 4

HCID 8028Tetrahydrofuran2회HCID 11776Triphenylphosphine3회HCID 220568ethyl N-ethoxycarbonyliminocarbamate3회HCID 66880246HCID 66880246, 화합물

생성물 1

HCID 668798542-(Pyridin-4-yl)-5-(trifluoromethoxy)benzoxazole

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

실험 절차

To a mixture of 1.96 g of N-[5-(trifluoromethoxy)-2-hydroxyphenyl]isonicotinamide, 35 ml of tetrahydrofuran and 1.73 g of triphenylphosphine, a mixture of 1.26 g of diethyl azodicarboxylate and 5 ml of THF was added dropwise at room temperature. The resultant mixture was stirred at room temperature for two hours. To the mixture, 1.73 g of triphenylphosphine and 3.15 g of 40% toluene solution of diethyl azodicarboxylate were added and stirred for one hour. Furthermore, to the mixture, 0.58 g of triphenylphosphine and 1.05 g of 40% toluene solution of diethyl azodicarboxylate were added and stirred for one hour. The mixture solution was poured into water, followed by extraction with ethyl acetate. The combined organic layers were washed with water and a saturated sodium chloride solution, and dried over magnesium sulfate. The reaction mixture was concentrated. The residue was subjected to silica gel column chromatography to give 2-(pyridin-4-yl)-5-(trifluoromethoxy)benzoxazole (hereinafter, referred to as “active compound 12”).

후처리

  1. additionwas added dropwise at room temperature
  2. stirringstirred for one hour
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. dry with materiala saturated sodium chloride solution, and dried over magnesium sulfate
  6. concentrationThe reaction mixture was concentrated

출처 및 근거

ORD 기록
ord-bad515c50c584d44a18c1ce726a93a50
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242133B2

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