Trimethylsilyl cyanide → HCID 89702355, compound

HRID 2202912Notes

Reaction equation

HRID 2202912 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)=[CH:13][C:12]3=[O:26])=[CH:7][N:6]2[C:27]=1[CH3:28].C[Si]([C:33]#[N:34])(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][O:17][C:14]2[CH:15]=[CH:16][N:11]([C:8]3[CH:9]=[CH:10][C:5]4[N:6]([C:27]([CH3:28])=[C:3]([CH2:2][C:33]#[N:34])[N:4]=4)[CH:7]=3)[C:12](=[O:26])[CH:13]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 121386210HCID 121386210, compound

Product 1

HCID 89702355HCID 89702355, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(2-(chloromethyl)-3-methylimidazo[1,2-a]pyridin-6-yl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (150 mg) in THF (5 ml) were added trimethylsilyl cyanide (115 μl) and TBAF (1 M in THF, 1.13 ml) at room temperature, and the resulting mixture was stirred at room temperature for 4 h. The reaction mixture was then quenched with saturated FeSO4, and the organic layer was extracted with DCM. The extract was washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel column chromatography (MeOH/DCM) to give the title compound (60 mg) as a white solid.

Workup

  1. customThe reaction mixture was then quenched with saturated FeSO4
  2. extractionthe organic layer was extracted with DCM
  3. washThe extract was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-0f5815b6cff2462588029952f26d0c99
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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