3-Fluoropyridine-4-carboxylic acid → HCID 77104946, compound

HRID 63073Notes

Reaction equation

HRID 63073 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][NH2:12])[CH2:3][CH2:2]1.F[C:14]1[CH:22]=[N:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]>>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH: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])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 3453613-Fluoropyridine-4-carboxylic acidHCID 133627273,4-dihydro-2H-1-benzopyran-4-ylmethanamine

Product 1

HCID 77104946HCID 77104946, compoundYield 13%

Procedure

The title compound was prepared in 13% yield from 1-(3,4-dihydro-2H-chromen-4-yl)methanamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 53. 1H NMR (400 MHz, DMSO-d6): δ 8.33 (s, 1H), 7.78 (d, 1H, J=5.0 Hz), 7.74 (br s, 1H), 7.50 (d, 1H, J=5.0 Hz), 7.23 (d, 1H, J=7.4 Hz), 7.04 (t, 1H, J=7.1 Hz), 6.78 (t, 1H, J=7.3 Hz), 6.69 (d, 1H, J=8.0 Hz), 4.06-4.17 (m, 2H), 3.59-3.65 (m, 1H), 3.41-3.47 (m, 1H), 3.04-3.09 (m, 1H), 1.79-1.96 (m, 2H). [M+H] calc'd for C16H16N2O3, 285. found 285.

Sources & evidence

ORD record
ord-67c28d40f51a4c44a923222b2d266c4c
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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