Cyclohexanone → HCID 9862693, compound

HRID 2294161Notes

Reaction equation

HRID 2294161 reaction equation
C[O-].[Na+].[C:4]([C:6]1[CH:23]=[CH:22][C:9]2[N:10]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][CH:17]=[CH:16]4)[CH:11]=[N:12][C:8]=2[CH:7]=1)#[N:5].[C:24]1(=O)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>CN(C)C=O>[C:4]([C:6]1[CH:23]=[CH:22][C:9]2[N:10]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][CH:17]=[C:16]4[C:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]=3)[CH:11]=[N:12][C:8]=2[CH:7]=1)#[N:5]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 10942334Sodium MethoxideHCID 214741665-Cyano-1-(indol-5-yl)benzimidazole

Product 1

HCID 9862693HCID 9862693, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of sodium methoxide (0.25 g, 4.6 mmol, 3 equivalents), 5-cyano-1-(indol-5-yl)benzimidazole (0.40 g, 1.54 mmol), and cyclohexanone (0.175 mL, 1.69 mmol, 1.1 equivalents) in N,N-dimethylformamide (8 mL) was heated at 130° C. under nitrogen for 12 hours. The solvent was removed by evaporation under reduced pressure, and the residue was partitioned between ethyl acetate (25 mL) and water (25 mL). The organic layer was separated, dried (MgSO4), and evaporated under reduced pressure. Column chromatography of the residue (0.16 g) using silica gel (approximately 5 g) and elution with ethyl acetate/hexanes [1:1] afforded the title compound. (19%) as a pale yellow solid. Rf =0.3 in ethyl acetate/hexanes [1:1]; 1H NMR (CDCl3) δ10.35 (br s, 1H), 8.18 (s, 1H), 8.05 (s, 1H), 7.80 (s, 1H), 7.45-7.43 (m, 3H), 7.21 (s, 1H), 7.07 (dd, J=8.5 and 1.9 Hz, 1H), 6.04 (br m, 1H), 2.32 (br m, 2H), 2.08 (br m, 2H), 1.72-1.60 (m, 2H), 1.60-1.50 (m, 2H); 13C NMR (CDCl3) δ145.7, 142.4, 137.5, 136.7, 130.9, 126.8, 125.7, 124.8, 123.8, 123.6. 122.5, 119.5, 119.2, 118.2, 117.2, 112.7, 112.1, 105.6, 28.4, 25.5, 22.9, 22.2.

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (25 mL) and water (25 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. washsilica gel (approximately 5 g) and elution with ethyl acetate/hexanes [1:1]

Sources & evidence

ORD record
ord-ca9b06cede504ab18e0edfc3c23bb65c
Source dataset
uspto-grants-1997_11
Patent number
US05688809

Reaction notes

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