3-Fluoropyridine-4-carboxylic acid → 3-[(4-Phenoxybenzyl)amino]pyridine-4-carboxylic acid

HRID 63045Notes

Reaction equation

HRID 63045 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH2:12][NH2:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:17]1[CH:25]=[N:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20]>>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([CH2:12][NH:13][C:22]2[CH:23]=[N:24][CH:25]=[CH:17][C:18]=2[C:19]([OH:21])=[O:20])=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 3453613-Fluoropyridine-4-carboxylic acidHCID 2760343(4-Phenoxyphenyl)methanamine

Product 1

HCID 867281993-[(4-Phenoxybenzyl)amino]pyridine-4-carboxylic acidYield 36%

Procedure

The title compound was prepared in 36% yield from 4-phenoxybenzylamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 13.42 (br s, 1H), 8.18 (s, 1H), 7.83 (d, 1H, J=5.0 Hz), 7.57 (d, 1H, J=5.0 Hz), 7.35-7.40 (m, 4H), 7.13 (t, 1H, J=7.2), 6.97-7.02 (m, 4H), 4.55 (s, 2H). [M+H] calc'd for C19H16N2O3, 321. found 321.

Sources & evidence

ORD record
ord-0bd1d95c328c427793bf4c5df71f66a9
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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