HCID 62952701, compound → 1-(5-Bromopyridin-2-yl)ethan-1-one

HRID 510990Notes

Reaction equation

HRID 510990 reaction equation
[CH3:1][Mg]Cl.[Br:4][C:5]1[CH:6]=[CH:7][C:8]([C:11](N(OC)C)=[O:12])=[N:9][CH:10]=1>C1COCC1>[Br:4][C:5]1[CH:6]=[CH:7][C:8]([C:11](=[O:12])[CH3:1])=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 62952701HCID 62952701, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 231453451-(5-Bromopyridin-2-yl)ethan-1-oneYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.0 M Methylmagnesium chloride in THF (0.5 mL) was added dropwise to a mixture of 5-bromo-N-methoxy-N-methylpyridine-2-carboxamide (200 mg, 0.8 mmol) in THF (10 mL) at 0° C. After stirring for 1 h at room temperature, the reaction was quenched with 1 N NH4Cl and was extracted with EtOAc. The combined organic layer was washed with brine and dried over MgSO4, concentrated to give the crude product (0.15 g, 90%). This was used in the next step without purification. LCMS calculated for C7H7BrNO (M+H)+: m/z=199.9, 201.9. found: 199.9, 201.9.

Workup

  1. customthe reaction was quenched with 1 N NH4Cl
  2. extractionwas extracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-501ad7b5cf544131b9516ea35bea00e8
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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