Potassium Carbonate → 1-[4-(Tert-butoxycarbonyl)phenyl]-2-cyanoindole

HRID 1769199Notes

Reaction equation

HRID 1769199 reaction equation
[C:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)#[N:2].[C:12]([O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][C:21](F)=[CH:20][CH:19]=1)([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:12]([O:16][C:17]([C:18]1[CH:23]=[CH:22][C:21]([N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:11]=[C:3]2[C:1]#[N:2])=[CH:20][CH:19]=1)=[O:25])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2736444Tert-butyl 4-fluorobenzoateHCID 37875991H-indole-2-carbonitrile

Product 1

HCID 103360241-[4-(Tert-butoxycarbonyl)phenyl]-2-cyanoindoleYield 55%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3.0 g (0.02 mol) of 2-cyanoindole, 4.2 g (0.02 mol) of tert-butyl-4-fluorobenzoate, and 5.5 g (0.04 mol) of potassium carbonate in 30 ml dimethyl sulfoxide was heated at 110° C. for 48 hours. The reaction was poured onto ice-water and extracted twice with ethyl acetate. The organic extracts were combined, washed with water and dried over magnesium sulfate. Evaporation yielded a dark oil which was flash chromatographed on silica gel, eluting with ethyl acetate-hexane 1:9 to give 3.6 g (0.011 mol) of 1-[4-(tertbutoxycarbonyl)phenyl]-2-cyanoindole as an oil.

Workup

  1. additionThe reaction was poured onto ice-water
  2. extractionextracted twice with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation
  6. customyielded a dark oil which
  7. customchromatographed on silica gel
  8. washeluting with ethyl acetate-hexane 1:9

Sources & evidence

ORD record
ord-8aa49e86ba7644bb9c69799091ad2349
Source dataset
uspto-grants-1995_01
Patent number
US05380739

Reaction notes

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