Acetone → 2-(6-Bromo-5-methoxypyridin-2-yl)propan-2-ol

HRID 658086

Reaction equation

HRID 658086 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4](I)[N:3]=1.C([Li])CCC.[CH3:16][C:17]([CH3:19])=[O:18].O>C1(C)C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[Br:1][C:2]1[N:3]=[C:4]([C:17]([OH:18])([CH3:19])[CH3:16])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

8

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 110990402-Bromo-6-iodo-3-methoxypyridineHCID 178418339Butyllithium

Product 1

HCID 575560732-(6-Bromo-5-methoxypyridin-2-yl)propan-2-ol

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-6-iodo-3-methoxy-pyridine (500 mg) is dissolved in dry toluene (5 ml) and thereto is added dropwise 1.6M n-butyllithium in hexane (1 ml) at −78° C. under nitrogen atmosphere, and the mixture is stirred for 1 hour and thereto is added acetone (0.23 ml), and the mixture is stirred overnight. To the reaction solution are added water and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→6:2) to give 2-(6-bromo-5-methoxy-pyridin-2-yl)-propan-2-ol (197 mg). MS (m/z): 246/248 [M+H]+

Workup

  1. stirringthe mixture is stirred overnight
  2. customthe mixture is separated
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→6:2)

Sources & evidence

ORD record
ord-1f6e356549924bf58356ad7926f353d7
Source dataset
uspto-grants-2011_12
Patent number
US08076364B2

Linked notes

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