tert-Butyl carbamate → tert-Butyl (5-fluoro-6-methylpyridin-2-yl)carbamate
Reaction equation
CC(C)(C)OC(N)=O.Cc1nc(Cl)ccc1F>CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=P([O-])([O-])[O-].[K+].[K+].[K+].[Pd].[Pd]>Cc1nc(NC(=O)OC(C)(C)C)ccc1FParticipants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 6-chloro-3-fluoro-2-methylpyridine (500 mg, 3.43 mmol), tert- Butyl carbamate (523 mg, 4.47 mmol), Potassium phosphate (1094 mg, 5.15 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (99 mg, 0.17 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (79 mg, 0.09 mmol) were combined in a sealed vial which was purged with nitrogen. Degassed toluene (5 mL) and water (5.00 mL) were added and the mixture was stirred under a nitrogen atmosphere at 90 °C for 6h. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 solution, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with mixtures of 5-50%EtOAc in heptane. Many spots isolated, but none of them seemed to be the desired product. Not continued.
Sources & evidence
- ORD record
- ord-849a1d763cb042f7907069ab25fe470c
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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