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

HRID 2190708ノート

反応式

HRID 2190708 の反応式
[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

参加物

7

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 11776Triphenylphosphine3 回HCID 220568ethyl N-ethoxycarbonyliminocarbamate3 回HCID 66880246HCID 66880246、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

実験手順

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”).

後処理

  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

出典と根拠

ORDレコード
ord-00730bcd9433422a97d7921ed737737b
出典データセット
uspto-grants-2012_12
特許番号
US08324387B2

反応ノート

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