2,6-Dichloro-N-methoxy-N-methylpyridine-3-carboxamide → (2,6-Dichloro-pyridin-3-yl)-(2-methoxy-phenyl)-methanone

HRID 30100Notes

Reaction equation

HRID 30100 reaction equation
[Cl:1][C:2]1[N:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:3]=1[C:4](N(OC)C)=[O:5].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Li]>O1CCCC1>[Cl:1][C:2]1[C:3]([C:4]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH3:15])=[O:5])=[CH:10][CH:11]=[C:12]([Cl:14])[N:13]=1

Participants

4

Reactant 2

HCID 534034112,6-Dichloro-N-methoxy-N-methylpyridine-3-carboxamideHCID 178506687HCID 178506687, compound

Product 1

HCID 59789365(2,6-Dichloro-pyridin-3-yl)-(2-methoxy-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2,6-Dichloro-N-methoxy-N-methyl-nicotinamide (503.3 mg, 2.141 mmol, Example 1) in anhydrous tetrahydrofuran (8 mL) was added a solution of freshly prepared 2-methoxyphenyl lithium (3-5 equiv, from above) and the reaction was stirred at −78° C. for 30-60 mins until the complete consumption of starting material. The resulting mixture was quenched with aqueous ammonium chloride solution, extracted with ethyl acetate, washed with saturated sodium chloride, dried over sodium sulfate and evaporated in vacuo. The residue was purified on silica gel with hexanes/ethyl acetate to give (2,6-Dichloro-pyridin-3-yl)-(2-methoxy-phenyl)-methanone as a light brown waxy solid (314.3 mg, 52% yield). HRMS, observed: 281.0023, Calcd for M+: 281.0010.

Workup

  1. customThe resulting mixture was quenched with aqueous ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified on silica gel with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-2f53521dbb114570a3c6959688798de8
Source dataset
uspto-grants-2008_09
Patent number
US07423051B2

Reaction notes

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