3-Fluoropyridine-4-carboxylic acid → 3-[(1-Benzofuran-3-ylmethyl)amino]pyridine-4-carboxylic acid

HRID 1525720Notes

Reaction equation

HRID 1525720 reaction equation
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([CH2:11][NH2:12])=[CH:3]1.F[C:14]1[CH:22]=[N:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]>>[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([CH2:11][NH:12][C:19]2[CH:20]=[N:21][CH:22]=[CH:14][C:15]=2[C:16]([OH:18])=[O:17])=[CH:3]1

Participants

3

Reactant 2

HCID 3453613-Fluoropyridine-4-carboxylic acidHCID 54593355HCID 54593355, compound

Product 1

HCID 867282093-[(1-Benzofuran-3-ylmethyl)amino]pyridine-4-carboxylic acidYield 8%

Procedure

The title compound was prepared in 8% yield from (1-benzofuran-3-yl)methylamine hydrochloride and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 5. 1H NMR (400 MHz, DMSO-d6): δ 13.39 (br s, 1H), 8.33 (s, 1H), 7.97 (s, 1H), 7.77 (d, 1H, J=5.0 Hz), 7.68 (br s, 1H), 7.57 (d, 1H, J=7.6 Hz), 7.48-7.52 (m, 2H), 7.17-7.28 (m, 2H), 4.64 (s, 2H). [M+H] calc'd for C15H12N2O3, 267; found 267.

Sources & evidence

ORD record
ord-8a5b27ebb58d4aacbde1d3d913ce72db
Source dataset
uspto-grants-2015_07
Patent number
US09085534B2

Reaction notes

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