Methyl 3-bromoisonicotinate → Methyl 3-({2-[(dimethylamino)methyl]benzyl}amino)pyridine-4-carboxylate
Reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[CH2:5][N:6]([CH3:8])[CH3:7].Br[C:14]1[CH:23]=[N:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]>>[CH3:7][N:6]([CH2:5][C:4]1[CH:9]=[CH:10][CH:11]=[CH:12][C:3]=1[CH2:2][NH:1][C:20]1[CH:21]=[N:22][CH:23]=[CH:14][C:15]=1[C:16]([O:18][CH3:19])=[O:17])[CH3:8]Participants
3
Procedure
The title compound was prepared in 65% yield from N-[2-(aminomethyl)benzyl]-N,N-dimethylamine and methyl 3-bromoisonicotinate according to the procedure for Preparation 4A. 1H NMR (400 MHz, CDCl3): δ 8.27 (s, 1H), 7.88 (d, 1H, J=5.1 Hz), 7.82 (br s, 1H), 7.61 (d, 1H, J=5.1 Hz), 7.20-7.36 (m, 4H), 4.68 (d, 2H, J=5.8 Hz), 3.87 (s, 3H), 3.46 (s, 2H), 2.22 (s, 6H). [M+H] calc'd for C17H21N3O2, 300. found 300.
Sources & evidence
- ORD record
- ord-0e283a2b457243298e84e39a3a18f11b
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447045B2
Reaction notes
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