Sodium Carbonate → HCID 86663047, compound
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[Na+].[Na+].[NH2:19][C:20]1[C:29](Br)=[N:28][C:27]([Br:31])=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23]>>[NH2:19][C:20]1[C:29]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[N:28][C:27]([Br:31])=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23]Participants
4
Conditions
- Temperature
- 110 °C
Procedure
A flask containing a mixture of 4-nitrophenylboronic acid (5.5 g, 32 9 mmol), sodium carbonate (10.3 g, 97 mmol), tetrakistriphenyphosphine palladium(0) (1.86 g, 1.61 mmol), and methyl 3-amino-2,6-dibromoisonicotinate (10 g, 32 3 mmol) was flushed with nitrogen, 1,4-dioxane (60.0 mL) followed by methanol (20 mL) were added, and the reaction heated at 110° C. for 16 h. The reaction mixture was partitioned between EtOAc and water. The organic phase was washed with sat. aq. Sodium bicarbonate solution and brine, dried with sodium sulfate, and the solvents removed. The residue was suspended and a mixture of EtOAc:hexane=1:4 and then filtered to give methyl 3-amino-6-bromo-2-(4-nitrophenyl)isonicotinate (9.3 g, 21 mmol, 66% yield). MS (ESI) m/z 354.04 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 8.37 (2 H, d, J=8.85 Hz), 7.91 (1H, s), 7.88 (2H, d, J=8.85 Hz), 5.98 (2H, br. s.), 3.98 (3H, s).