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

HRID 514340Notes

Reaction equation

HRID 514340 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-397cb92814b84e37a09425fcaf3d0664
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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