3-Bromo-5-methylpyridine → 1-(5-Methylpyridin-3-yl)ethan-1-one

HRID 595041Notes

Reaction equation

HRID 595041 reaction equation
BrC1[CH:3]=[N:4][CH:5]=C(C)C=1.CON(C)[C:12](=[O:14])[CH3:13].[Li][CH2:17][CH2:18][CH2:19][CH3:20]>C(OCC)C>[CH3:20][C:19]1[CH:18]=[C:17]([C:12](=[O:14])[CH3:13])[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 8177133-Bromo-5-methylpyridineHCID 178502655HCID 178502655, compound

Product 1

HCID 5775691-(5-Methylpyridin-3-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To 3-bromo-5-methylpyridine 1-1 (2 g, 11.63 mmol) in diethyl ether (30 ml) at −78° C. was added uLi (8.72 ml, 13.95 mmol) dropwise. After 30 min, N-methoxy-N-methylacetamide n-BuLi was added. The resulting mixture was stirred at −78° C. for 2 h then at rt overnight, quenched with saturated NH4Cl solution and diluted with EtOAc. The organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to give a yellow residue, which was purified by column chromatography (0-65% EtOAc in hexane) to give the desired product 1-2: 1H NMR (400 MHz, CDCl3) δ 8.98 (s, 1H), 8.62 (s, 1H), 8.04 (s, 1H), 2.63 (s, 3H), 2.41 (s, 3H).

Workup

  1. customat rt overnight, quenched with saturated NH4Cl solution
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give a yellow residue, which
  7. customwas purified by column chromatography (0-65% EtOAc in hexane)

Sources & evidence

ORD record
ord-b7d8f71043c243d7a29a2a1562dd9f14
Source dataset
uspto-grants-2016_01
Patent number
US09242995B2

Reaction notes

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