Dimethylformamide → 4-[1-(4-Trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]-benzonitrile

HRID 62065노트

반응식

HRID 62065 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[CH:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[CH3:24][N:25](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:21][C:20]([F:23])([F:22])[O:19][C:16]1[CH:17]=[CH:18][C:13]([N:10]2[CH:11]=[N:12][C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:24]#[N:25])=[CH:3][CH:4]=3)=[N:9]2)=[CH:14][CH:15]=1

참가 물질

6

반응물 2

HCID 6228DimethylformamideHCID 904040773-(4-bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1 H-1,2,4-triazole

생성물 1

HCID 669571074-[1-(4-Trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]-benzonitrile수율 94%

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

In a 250 mL flask, 3-(4-bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (4.00 g, 10.4 mmol) was dissolved in N,N-dimethylformamide (30 mL) under nitrogen atmosphere. Zinc cyanide (1.46 g, 12.4 mmol) and tetrakis(triphenylphosphine) palladium(0) (0.601 g, 0.0500 mmol) were added and the reaction mixture was heated to 110° C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with water. The aqueous layer was further extracted with ethyl acetate. The combined organics were washed with water and brine, dried over magnesium sulfate and concentrated. Purification by flash column chromatography eluting with 30% ethyl acetate/hexanes gave the title compound as off-white solid (3.40 g, 94%): mp 172-176° C.; 1H NMR (400 MHz, CDCl3): δ 8.60 (s, 1H), 8.31 (d, J=8.8 Hz, 2H), 7.81 (d, J=8.8 Hz, 2H), 7.77 (d, J=8.8 Hz, 2H), 7.41 (d, J=8.8 Hz, 2H); ES+API m/z 331 ([M+H]+).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water
  3. extractionThe aqueous layer was further extracted with ethyl acetate
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customPurification by flash column chromatography
  8. washeluting with 30% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-6923f5cd857b4c6c972bc13a2d4e7a77
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09445594B2

반응 노트

불러오는 중…