(2E)-3-(dimethylamino)-1-(3-methoxyphenyl)prop-2-en-1-one → 2-(5-(3-methoxyphenyl)-1H-pyrazol-1-yl)pyridine-4-carbonitrile

HRID 878508Notes

Reaction equation

HRID 878508 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][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)=O>>[CH3:25][O:24][C:20]1[CH:19]=[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:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 12233520(2E)-3-(dimethylamino)-1-(3-methoxyphenyl)prop-2-en-1-oneHCID 867254842-Hydrazinylpyridine-4-carbonitrile hydrochloride salt

Product 1

HCID 867254892-(5-(3-methoxyphenyl)-1H-pyrazol-1-yl)pyridine-4-carbonitrileYield 98%

Procedure

The title compound was prepared in 98% yield from 2-hydrazinylpyridine-4-carbonitrile hydrochloride salt (PREPARATION 3) and (2E)-3-(dimethylamino)-1-(3-methoxyphenyl)prop-2-en-1-one according to the procedure for the preparation of Example 12, part B. 1H NMR (400 MHz, CDCl3): δ 3.78 (3H, s), 6.53 (1H, s), 6.81-6.85 (2H, m), 6.90-6.93 (1H, m), 7.24-7.28 (1H, m), 7.38 (1H, dd, J=5.6, 1.2 Hz), 7.77 (1H, d, J=2.0 Hz), 7.93 (1H, s), 8.44 (1H, dd, J=5.2, 0.8 Hz).

Sources & evidence

ORD record
ord-bc58b2ae3f464037a489b0713dc8adaa
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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