Sodium Carbonate → HCID 86663040, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[NH2:11][C:12]1[C:21](Br)=[N:20][C:19]([Br:23])=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[Na+].[Na+]>>[NH2:11][C:12]1[C:21]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:20][C:19]([Br:23])=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15]Participants
Conditions
- Temperature
- 93 °C
Procedure
A mixture of 4-chlorophenylboronic acid (3.03 g, 19.4 mmol), methyl 3-amino-2,6-dibromoisonicotinate (5.0 g, 16 1 mmol), tetrakistriphenylphosphine palladium (0) (1.12 g, 0.968 mmol), sodium carbonate (4.10 g, 38 7 mmol) was flushed with nitrogen, toluene (40 mL), and MeOH (13 mL) were added and the reaction was heated in a 93° C. for 30 hr. This was partitioned between EtOAc and water and the organic phase was washed with brine, dried with sodium sulfate, and the solvent removed. Silica gel chromatography (step gradient elution with DCM containing 75 to 0% hexane) afforded methyl 3-amino-6-bromo-2-(4-chlorophenyl)isonicotinate (3.86 g, 11 3 mmol, 70% yield) as a yellow fluffy solid. MS (ESI) m/z 343.02 (M+H). 1 H NMR (500 MHz, chloroform-d) δ ppm 7.81 (1H, s), 7.54-7.60 (2H, m), 7.43-7.49 (2H, m), 5.91 (2H, br.s.), 3.93 (3H, s).
Workup
- customwas flushed with nitrogen, toluene (40 mL), and MeOH (13 mL)
- additionwere added
- customThis was partitioned between EtOAc and water
- washthe organic phase was washed with brine
- dry with materialdried with sodium sulfate
- customthe solvent removed
- washSilica gel chromatography (step gradient elution with DCM containing 75 to 0% hexane)
Sources & evidence
- ORD record
- ord-12763fb5959f48d9bf9af5ec889efb82
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815840B2
Reaction notes
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