3-Bromopyridine → tert-Butyl [2-oxo-2-(pyridin-3-yl)ethyl]carbamate

HRID 1354402Notes

Reaction equation

HRID 1354402 reaction equation
C([Mg]Br)(C)C.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.COCN[C:17](=[O:27])[CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23]>C1COCC1>[O:27]=[C:17]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25]

Participants

5

Reactant 3

HCID 122863-BromopyridineHCID 21105795tert-Butyl {2-[(methoxymethyl)amino]-2-oxoethyl}carbamateHCID 178418365HCID 178418365, compound

Product 1

HCID 58993194tert-Butyl [2-oxo-2-(pyridin-3-yl)ethyl]carbamateYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Isopropylmagnesium bromide (15.5 ml, 2M in THF) was added to a solution of 3-bromopyridine (4.92 g) in THF (30 ml) at 0° C. and stirred for 1 h. A solution of the product from step (a) (2.18 g) in THF (20 ml) was then added and the reaction mixture was stirred at room temperature for 40 h. The mixture was quenched by the addition of saturated ammonium chloride solution (250 ml) and extracted with ethyl acetate. The organic layer was washed with brine and dried (MgSO4). The solvent was evaporated off and the residue purified by chromatography (silica, 20% ethyl acetate/dichloromuethane as eluent) to give the sub-title compound (1.84 g) as a white solid.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 40 h
  2. customThe mixture was quenched by the addition of saturated ammonium chloride solution (250 ml)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated off
  7. customthe residue purified by chromatography (silica, 20% ethyl acetate/dichloromuethane as eluent)

Sources & evidence

ORD record
ord-30105fd64fef4b76bc991af302cdd4fb
Source dataset
uspto-grants-2007_05
Patent number
US07223794B2

Reaction notes

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