4-(Trifluoromethyl)benzylamine → Methyl 3-{[4-(trifluoromethyl)benzyl]amino}pyridine-4-carboxylate

HRID 63040Notes

Reaction equation

HRID 63040 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.Br[C:14]1[CH:23]=[N:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]>>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:20]2[CH:21]=[N:22][CH:23]=[CH:14][C:15]=2[C:16]([O:18][CH3:19])=[O:17])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 768044-(Trifluoromethyl)benzylamineHCID 2762700Methyl 3-bromoisonicotinate

Product 1

HCID 86728196Methyl 3-{[4-(trifluoromethyl)benzyl]amino}pyridine-4-carboxylateYield 40%

Procedure

The title compound was prepared in 40% yield from 4-(trifluoromethyl)benzylamine and methyl 3-bromoisonicotinate according to the procedure for Preparation 4A. 1H NMR (400 MHz, CDCl3): δ 8.12 (s, 1H), 7.95 (d, 1H, J=5.0 Hz), 7.93 (br s, 1H), 7.65 (d, 1H, J=5.0 Hz), 7.60 (d, 2H, J=8.1 Hz), 7.47 (d, 2H, J=8.1 Hz), 4.58 (d, 2H, J=5.9 Hz) 3.91 (s, 3H). [M+H] calc'd for C15H13F3N2O2, 311. found 311.

Sources & evidence

ORD record
ord-db6772170dae49b484a79adf737b0802
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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