N-methoxy-N-methylimidazo[1,2-a]pyridine-7-carboxamide → 1-Imidazo[1,2-a]pyridin-7-yl-but-2-yn-1-one

HRID 341208Notes

Reaction equation

HRID 341208 reaction equation
CON(C)[C:4]([C:6]1[CH:11]=[CH:10][N:9]2[CH:12]=[CH:13][N:14]=[C:8]2[CH:7]=1)=[O:5].[C:16]([Mg]Br)#[C:17][CH3:18]>C1COCC1>[N:14]1[CH:13]=[CH:12][N:9]2[CH:10]=[CH:11][C:6]([C:4](=[O:5])[C:16]#[C:17][CH3:18])=[CH:7][C:8]=12

Participants

4

Reactant 2

HCID 59320928N-methoxy-N-methylimidazo[1,2-a]pyridine-7-carboxamideHCID 178419101HCID 178419101, compound

Product 1

HCID 593208621-Imidazo[1,2-a]pyridin-7-yl-but-2-yn-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Imidazo[1,2-a]pyridine-7-carboxylic acid methoxy-methyl-amide (187 mg, 0.91 mmol) in THF (10 ml) at −78° C. was added 1-propynylmagnesium bromide (0.5M in THF, 2.74 ml). The reaction was allowed to warm to room temperature and stirred for 1.5 h before being quenched with 2M HCl (2 ml) and washed with CH2Cl2. The aqueous fraction was basified using Na2CO3 and extracted with CH2Cl2. The organic fraction was dried (MgSO4), filtered and the solvent removed in vacuo to afford the product (168 mg). MS: [M+H]+=185.

Workup

  1. custombefore being quenched with 2M HCl (2 ml)
  2. washwashed with CH2Cl2
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic fraction was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d497164cb296465ba948d887b72b4e12
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

Loading…