3-Fluoropyridine-4-carboxylic acid → 3-[(2,4-Dimethyoxybenzyl)amino]pyridine-4-carboxylic acid

HRID 1847157Notes

Reaction equation

HRID 1847157 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].F[C:14]1[CH:22]=[N:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]>>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][C:19]1[CH:20]=[N:21][CH:22]=[CH:14][C:15]=1[C:16]([OH:18])=[O:17]

Participants

3

Reactant 2

HCID 3453613-Fluoropyridine-4-carboxylic acidHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 817535033-[(2,4-Dimethyoxybenzyl)amino]pyridine-4-carboxylic acidYield 61%

Procedure

The title compound was prepared in 61% yield from 2,4-dimethoxybenzylamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 13.41 (br s, 1H), 8.20 (s, 1H), 7.80 (d, 1H, J=5.0 Hz), 7.54 (d, 1H, J=5.0 Hz), 7.18 (d, 1H, J=8.3 Hz), 6.59 (d, 1H, J=2.4 Hz), 6.48 (dd, 1H, J=8.3, 2.4 Hz), 4.40 (s, 2H), 382 (s, 3H), 3.74 (s, 3H). [M+H] calc'd for C15H16N2O4, 259. Found 259.

Sources & evidence

ORD record
ord-1e5d5ca8e2d640f2b0ee7eb520f6100f
Source dataset
uspto-grants-2015_02
Patent number
US08952151B2

Reaction notes

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