Methylamine → 6-Bromo-N-methylpicolinamide
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.CN.C(C1NC=CN=1)([C:15]1[NH:16]C=CN=1)=O>>[CH3:15][NH:16][C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=1)=[O:10]Participants
4
Procedure
6-Bromopicolinic acid (Aldrich) was coupled with methyl amine using carbonyl diimidazole (CDI) as coupling reagent to afford 6-bromopyridine-2-carboxylic acid methylamide. The 6-bromopyridine-2-carboxylic acid methylamide underwent Suzuki coupling with 4-phenoxyphenylboronic acid, in the presence of tetrakis(triphenylphosphine)palladium as catalyst to give 6-(4-phenoxyphenyl)pyridine-2-carboxylic acid methylamide as a solid. 1H NMR (CDCl3): δ 8.12 (d, J=7.8 Hz, 1H), 7.98 (d, J=8.7 Hz, 2H), 7.90 (t, J=7.8 Hz, 1H), 7.81 (d, J=7.8 Hz, 1H), 7.38 (t, J=8.4 Hz, 2H), 7.18-7.06 (m, 5H), 3.08 (d, J=5.4 Hz, 3H).
Sources & evidence
- ORD record
- ord-68d2e711e1164a1580bb343cb4beadd0
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06867210B2
Reaction notes
Loading…