5-Butyl-pyridine-2-carboxylic acid methoxy-methyl-amide → 1-(5-Butyl-pyridin-2-yl)-ethanone

HRID 899310

Reaction equation

HRID 899310 reaction equation
[CH3:1][Mg+].[Br-].CON(C)[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH3:18])=[CH:11][N:10]=1)=[O:8]>C1COCC1>[CH2:15]([C:12]1[CH:13]=[CH:14][C:9]([C:7](=[O:8])[CH3:1])=[N:10][CH:11]=1)[CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 587470075-Butyl-pyridine-2-carboxylic acid methoxy-methyl-amideHCID 178418689HCID 178418689, compound

Product 1

HCID 124362861-(5-Butyl-pyridin-2-yl)-ethanoneYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

MeMgBr (1.98 ml, 5.94 mmol) was added to a solution of 5-butyl-pyridine-2-carboxylic acid methoxy-methyl-amide (I-2A-38a; 880 mg, 3.96 mmol) in THF (10 ml) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred for 1.5 h, quenched with saturated aqueous NH4Cl (1 ml), and saturated aqueous NaCl. The aqueous THF solution was extracted with EtOAc (2×), and the combined organic extracts were washed with saturated aqueous NaCl, dried, and concentrated under vacuum to yield the product I-2A-38b as an oil (680 mg): APcl MS 178.1 (M+1)+; 1H NMR (400 MHz, CDCl3) δ 8.47 (d, 1H, J=1.6 Hz), 7.95 (d, 1H, J=8.3 Hz), 7.60 (dd, 1H, J=1.6, 8.3 Hz), 2.69 (s, 3H), 2.67 (t, 2H, J=7.9 Hz), 1.65-1.56 (m, 2H), 1.40-1.30 (m, 2H), 0.92 (t, 3H, J=7.4 Hz).

Workup

  1. customquenched with saturated aqueous NH4Cl (1 ml), and saturated aqueous NaCl
  2. extractionThe aqueous THF solution was extracted with EtOAc (2×)
  3. washthe combined organic extracts were washed with saturated aqueous NaCl
  4. customdried
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-902078b39d794527b161f59d8e141b6a
Source dataset
uspto-grants-2008_04
Patent number
US07354929B2

Linked notes

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