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

HRID 1913613

반응식

HRID 1913613 반응식
[Br:1][C:2]1[CH:21]=[N:20][CH:19]=[CH:18][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=1[OH:17])=O.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>[Br:1][C:2]1[CH:21]=[N:20][CH:19]=[CH:18][C:3]=1[C:4]1[O:17][C:8]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]=2[N:6]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 668798803-bromo-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide

생성물 1

HCID 668809172-(3-Bromopyridin-4-yl)-5-(trifluoromethyl)benzoxazole수율 87.1%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
50 °C

실험 절차

To a mixture of 0.29 g of 3-bromo-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide, 4 ml of tetrahydrofuran and 0.25 g of triphenylphosphine, 0.42 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature. The reaction mixture was stirred while heating at 50° C. for 1.5 hours. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.24 g of 2-(3-bromopyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 27”).

후처리

  1. additionwas added dropwise at room temperature
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5086dda980724981977988f9deade821
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609705B2

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