HCID 121386206, compound → HCID 89690968, compound

HRID 2202929Notes

Reaction equation

HRID 2202929 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:14]3[CH:15]=[CH:16][C:17]4[N:18]([C:20]([CH3:29])=[C:21]([C:23](N(OC)C)=[O:24])[N:22]=4)[CH:19]=3)[C:10](=[O:30])[CH:9]=2)=[CH:4][CH:3]=1.[CH3:33][Mg]Br>C1COCC1>[C:23]([C:21]1[N:22]=[C:17]2[CH:16]=[CH:15][C:14]([N:11]3[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:32][CH:31]=4)=[CH:9][C:10]3=[O:30])=[CH:19][N:18]2[C:20]=1[CH3:29])(=[O:24])[CH3:33]

Participants

4

Reactant 2

HCID 121386206HCID 121386206, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 89690968HCID 89690968, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-(4-((4-fluorobenzyl)oxy)-2-oxopyridin-1(2H)-yl)-N-methoxy-N,3-dimethylimidazo[1,2-a]pyridine-2-carboxamide (150 mg) in THF (10 ml) was added methylmagnesium bromide (3 M ether solution, 344 μl) at −78° C., and the resulting mixture was stirred at the same temperature for 2 h. The reaction mixture was then quenched with saturated aqueous NH4Cl (40 ml) at −78° C., and slowly warmed to room temperature. The reaction mixture was concentrated in vacuo and diluted with EtOAc (100 ml). The EtOAc layer was washed with brine (40 ml), dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel column chromatography (MeOH/DCM) to give the title compound (55 mg) as a white solid.

Workup

  1. customThe reaction mixture was then quenched with saturated aqueous NH4Cl (40 ml) at −78° C.
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with EtOAc (100 ml)
  4. washThe EtOAc layer was washed with brine (40 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-1b6e5a99fcb645bf87ffa54b1ebf3156
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

Loading…