2-Bromo-6-methoxypyridine → [3-(6-Methoxy-2-pyridinyl)-3-oxopropyl]carbamic acid 1,1-dimethylethyl ester

HRID 2179960Notes

Reaction equation

C([Li])CCC.Br[C:7]1[N:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][CH:8]=1.[CH3:15][C:16]([O:19][C:20](=[O:30])[NH:21][CH2:22][CH2:23][C:24](NCOC)=[O:25])([CH3:18])[CH3:17]>O1CCCC1>[CH3:18][C:16]([O:19][C:20](=[O:30])[NH:21][CH2:22][CH2:23][C:24]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([O:13][CH3:14])[N:12]=1)=[O:25])([CH3:15])[CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

Butyl lithium (2.5M solution in hexanes, 1.4 ml) was added to a solution of 6-bromo-2-methoxypyridine (690 mg, 4.0 mmol) in tetrahydrofuran (4 ml) at −78° C. and stirred for 1 h. A solution of [3-(methoxymethylamino)-3-oxopropyl carbamic acid 1,1-dimethylethyl ester (344 mg, 1.42 mmol) in tetrahydrofuran (3 ml) was added and the mixture was warmed to 0° C. over 3 h. The mixture was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate (three times) The combined organic extracts were dried (sodium sulphate), evaporated and purified by chromatography on silica eluting with petrol-acetone to give the sub-title compound as a colourless oil (291 mg, 73%).

Workup

customThe mixture was quenched with saturated aqueous ammonium chloride
extractionextracted with ethyl acetate (three times) The combined organic extracts
dry with materialwere dried (sodium sulphate)
customevaporated
custompurified by chromatography on silica eluting with petrol-acetone

Sources & evidence

ORD record: ord-560ee9a45df445ab8891d4fb41f77028
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06887871B2

Reaction notes

Loading…