(2E)-3-(dimethylamino)-1-(4-methylphenyl)prop-2-en-1-one → 2-[5-(4-Methylphenyl)-1H-pyrazol-1-yl]pyridine-4-carbonitrile

HRID 514340

반응식

HRID 514340 반응식
Cl.[NH:2]([C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][N:5]=1)[NH2:3].CN(C)/[CH:14]=[CH:15]/[C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)=O>COCCO>[CH3:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]2[N:2]([C:4]3[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][N:5]=3)[N:3]=[CH:14][CH:15]=2)=[CH:19][CH:20]=1

참가 물질

4

반응물 2

HCID 5398494(2E)-3-(dimethylamino)-1-(4-methylphenyl)prop-2-en-1-oneHCID 867254842-Hydrazinylpyridine-4-carbonitrile hydrochloride salt

생성물 1

HCID 867254852-[5-(4-Methylphenyl)-1H-pyrazol-1-yl]pyridine-4-carbonitrile수율 92.2%

시약·촉매·용매 1

HCID 80192-Methoxyethanol용매

반응 조건

온도
100 °C

실험 절차

A mixture of 2-hydrazinylpyridine-4-carbonitrile hydrochloride salt (124 mg, 0.6 mmol, PREPARATION 3) and (2E)-3-(dimethylamino)-1-(4-methylphenyl)prop-2-en-1-one (95 mg, 0.5 mmol) in 2-methoxyethanol (3 mL) was stirred at 100° C. for 2 h. The reaction mixture was cooled, concentrated, and dissolved in EtOAc and then washed with water and brine. The organic phase was dried, concentrated, triturated with EA/PE (1:10, 5 mL), filtered, and dried to give the title compound (120 mg, 92%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 2.38 (3H, s), 6.49 (1H, d, J=1.6 Hz), 7.16 (4H, s), 7.38 (1H, dd, J=5.2, 1.2 Hz), 7.76 (1H, d, J=1.2 Hz), 7.90 (1H, s), 8.44 (1H, d, J=5.2 Hz).

후처리

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. dissolutiondissolved in EtOAc
  4. washwashed with water and brine
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. customtriturated with EA/PE (1:10, 5 mL)
  8. filtrationfiltered
  9. customdried

출처 및 근거

ORD 기록
ord-397cb92814b84e37a09425fcaf3d0664
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09107916B2

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