3-Ethyl-4-(hydroxymethyl)benzonitrile → Methyl 2-[5-[(4-cyano-2-ethylphenyl)methoxy]pyrazol-1-yl]pyridine-4-carboxylate

HRID 514506Notes

Reaction equation

HRID 514506 reaction equation
[OH:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][N:8]=2)[N:5]=[CH:4][CH:3]=1.[CH2:17]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[CH2:27]O)[C:22]#[N:23])[CH3:18]>>[C:22]([C:21]1[CH:24]=[CH:25][C:26]([CH2:27][O:1][C:2]2[N:6]([C:7]3[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][N:8]=3)[N:5]=[CH:4][CH:3]=2)=[C:19]([CH2:17][CH3:18])[CH:20]=1)#[N:23]

Participants

3

Reactant 2

HCID 249719563-Ethyl-4-(hydroxymethyl)benzonitrileHCID 178498428HCID 178498428, compound

Product 1

HCID 86725620Methyl 2-[5-[(4-cyano-2-ethylphenyl)methoxy]pyrazol-1-yl]pyridine-4-carboxylate

Procedure

The title compound was prepared from methyl 2-(5-hydroxypyrazol-1-yl)pyridine-4-carboxylate (PREPARATION 6) and 3-ethyl-4-(hydroxymethyl)benzonitrile according to the procedure for the preparation of Example 125, part B. 1H NMR (400 MHz, CDCl3): δ 1.26 (3H, t, J=7.6 Hz), 2.73 (2H, q, J=7.6 Hz), 3.96 (3H, s), 5.28 (2H, s), 5.77 (1H, d, J=1.2 Hz), 7.53-7.67 (4H, m), 7.77 (1H, d, J=4.8 Hz), 8.31 (1H, s), 8.67 (1H, d, J=4.8 Hz). [M+H] Calc'd for C20H18N4O3, 363. Found, 363.

Sources & evidence

ORD record
ord-7be403eba4f441f5becb95db6745ede1
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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