Water → HCID 86703315, compound

HRID 2409998Notes

Reaction equation

HRID 2409998 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].CC(C)([O-])C.[K+].[CH:18]([C:20]1[N:25]=[C:24]([CH2:26][C:27]2[C:35]3[C:30](=[CH:31][C:32]([O:36][CH3:37])=[CH:33][CH:34]=3)[N:29]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:28]=2[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:23]=[CH:22][CH:21]=1)=O.O>CS(C)=O.[Cl-].[Na+].O>[C:1](/[CH:3]=[CH:18]/[C:20]1[N:25]=[C:24]([CH2:26][C:27]2[C:35]3[C:30](=[CH:31][C:32]([O:36][CH3:37])=[CH:33][CH:34]=3)[N:29]([C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])[C:28]=2[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:23]=[CH:22][CH:21]=1)#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 75676Diethyl (cyanomethyl)phosphonateHCID 23665647Potassium tert-butoxideHCID 86703314HCID 86703314, compound

Product 1

HCID 86703315HCID 86703315, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of diethyl cyanomethylphosphonate (0.173 mL) in dimethylsulfoxide (6 mL) was added potassium tert-butoxide (127 mg) at room temperature, and the mixture was stirred for 30 minutes. Then a solution of tert-butyl 3-(6-formylpyridin-2-ylmethyl)-6-methoxy-2-phenyl-1H-indole-1-carboxylate (385 mg) in dimethylsulfoxide (3 mL) was added dropwise at room temperature, and the mixture was stirred overnight. To the reaction mixture were added water and saturated brine, followed by extraction with ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (192 mg). 1H-NMR (CDCl3) δ ppm: 1.23 (9H, s), 3.89 (3H, s), 4.04 (2H, s), 6.55 (1H, d, J=15.8 Hz), 6.82-6.90 (1H, m), 6.96-7.03 (1H, m), 7.04-7.12 (1H, m), 7.23-7.46 (7H, m), 7.48-7.57 (1H, m), 7.82-7.90 (1H, m).

Workup

  1. stirringthe mixture was stirred overnight
  2. extractionfollowed by extraction with ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with water and saturated brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-0a31f11f335e4c73ac0279e0ff255656
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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