HCID 121386212, compound → HCID 89691109, compound

HRID 2202997Notes

Reaction equation

HRID 2202997 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][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]([CH3:31])=[C:21]([CH:23]5[CH2:25][CH:24]5C(OCC)=O)[N:22]=4)[CH:19]=3)[C:10](=[O:32])[CH:9]=2)=[CH:4][CH:3]=1.C[Mg]Br>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][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]([CH3:31])=[C:21]([CH:23]5[CH2:25][CH:24]5[C:8]([OH:7])([CH3:13])[CH3:9])[N:22]=4)[CH:19]=3)[C:10](=[O:32])[CH:9]=2)=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 121386212HCID 121386212, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 89691109HCID 89691109, compoundYield 5.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 2-(6-(4-((4-chlorobenzyl)oxy)-2-oxopyridin-1(2H)-yl)-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxylate (250 mg) in THF (2 ml) was added methylmagnesium bromide (3.0 M solution in ether, 1.8 ml) at 0° C., and the resulting mixture was stirred at room temperature for 3 h. The reaction mixture was then quenched with saturated NH4Cl solution, and extracted with DCM. The extract was washed with brine, dried over Na2SO4, concentrated in vacuo and purified by column chromatography (MeOH/DCM) to afford the title compound (7 mg) as an off-white solid.

Workup

  1. customThe reaction mixture was then quenched with saturated NH4Cl solution
  2. extractionextracted with DCM
  3. washThe extract was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-702cd34ad05243f79b08ff509a0affa7
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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