Potassium Carbonate → Tert-butyl(6-bromo-3-methoxypyridin-2-yl)carbamate
Reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[C:18]([Br:24])[N:17]=1)C(OC(C)(C)C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CO>[C:1]([O:5][C:6](=[O:7])[NH:8][C:16]1[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[C:18]([Br:24])[N:17]=1)([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of the title compound and di-tert-butyl(6-bromo-3-methoxypyridin-2-yl)imidodicarbonate (7.19 g, approximate ratio of 43:57) in MeOH (55 mL) at rt was added K2CO3 (7.39 g, 53.5 mmol). After stirring at 55° C. for 1.5 h the mixture was cooled to rt and combined with a previous reaction mixture derived from title compound and di-tert-butyl(6-bromo-3-methoxypyridin-2-yl)imidodicarbonate (8.83 g, approximate ratio of 43:57) and filtered. The residue was washed with EtOAc and the filtrate was concentrated in vacuo. Purification by gradient flash chromatography, eluting with 10-25% EtOAc in heptane yielded the title compound (8.38 g, 27.6 mmol) as a pale yellow solid.
Sources & evidence
- ORD record
- ord-511dfeb2b31a4c97a82c76adda4dd268
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249160B2
Reaction notes
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