Tetrahydrofuran → 2-(3-Phenyl pyridin-4-yl)-5-(trifluoromethyl)benzoxazole

HRID 884852노트

반응식

HRID 884852 반응식
I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N:12]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O1CCCC1.[OH-].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:21]1([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=3[N:12]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66827Phenylboronic AcidHCID 668805972-(3-Iodopyridin-4-yl)-5-(trifluoromethyl)benzoxazole

생성물 1

HCID 668806132-(3-Phenyl pyridin-4-yl)-5-(trifluoromethyl)benzoxazole수율 26.5%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매

실험 절차

To a mixture of 0.78 g of 2-(3-iodopyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.27 g of phenylboronic acid, 5 ml of tetrahydrofuran and 0.14 g of dichlorobis(triphenylphosphine)palladium (II), 3 ml of 10% aqueous solution of sodium hydroxide was added and heated to reflux for three hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.18 g of 2-(3-phenyl pyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 32”).

후처리

  1. additionwas added
  2. temperatureheated
  3. temperatureto reflux for three hours
  4. extractionfollowed by extraction with ethyl acetate twice
  5. washThe combined organic layers were washed with water
  6. dry with materiala saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e1638b6e1f0d46db8c9e54c5b156f2e0
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242133B2

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