Ammonium Chloride → 1-(Thieno[3,2-c]pyridin-2-yl)ethanone

HRID 1890518Notes

Reaction equation

HRID 1890518 reaction equation
CON(C)[C:4]([C:6]1[S:14][C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[CH:7]=1)=[O:5].[CH3:16][Mg+].[Br-].[NH4+].[Cl-]>C1COCC1>[S:14]1[C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[CH:7]=[C:6]1[C:4](=[O:5])[CH3:16]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86671431N-Methoxy-N-methylthieno[3,2-c]pyridine-2-carboxamideHCID 178418689HCID 178418689, compound

Product 1

HCID 584330461-(Thieno[3,2-c]pyridin-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methoxy-N-methylthieno[3,2-c]pyridine-2-carboxamide (D′-2) (11.1 g, 50 mmol) in anhydrous THF (150 mL) was added MeMgBr (3M in ethyl ether, 25 mL, 75 mmol) at 0° C. under N2. The reaction mixture was allowed to warm to the ambient temperature and stirred overnight. Saturated aqueous NH4Cl solution was added to quench the reaction. The resulting mixture was then extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated to afford the title compound. MS (m/z): 178 (M+1)+.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe resulting mixture was then extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c8e67592481648318440fce596212dcf
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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