Phenyl isocyanate → benzenesulfonyl-5-[2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-ethyl]-1H-indole-2-carbonitrile

HRID 268900Notes

Reaction equation

HRID 268900 reaction equation
C([Li])(C)(C)C.[C:6]1([S:12]([N:15]2[C:23]3[C:18](=[CH:19][C:20]([CH:24]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])=[CH:21][CH:22]=3)[CH:17]=[CH:16]2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:40][N:41](C)CCN(C)C.C1(N=C=O)C=CC=CC=1>O1CCCC1>[C:6]1([S:12]([N:15]2[C:23]3[C:18](=[CH:19][C:20]([CH:24]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:28])[CH3:29])=[CH:21][CH:22]=3)[CH:17]=[C:16]2[C:40]#[N:41])(=[O:14])=[O:13])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 7672Phenyl isocyanateHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 598317081-benzenesulfonyl-5-[2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-ethyl]-1H-indoleHCID 178418306HCID 178418306, compound

Product 1

HCID 59831791benzenesulfonyl-5-[2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-ethyl]-1H-indole-2-carbonitrileYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyllithium (1.7 M in pentane, 3.42 mmol) was added at −78° C. to a mixture of 1-benzenesulfonyl-5-[2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-ethyl]-1H-indole CCLXVIII (865 mg, 1.71 mmol) and N,N,N′,N′-tetramethylethylenediamine (0.51 mL, 3.42 mmol) in tetrahydrofuran (20 mL). The resulting mixture was stirred for 1 hour and then a solution of phenyl isocyanate (300 mg, 2.565 mmol) in tetrahydrofuran (2 mL) was added dropwise at −78° C. The resulting mixture was stirred at −78° C. for 1.5 hour and at 0° C. for 1.5 hours. The reaction was then quenched by addition of a saturated aqueous solution of ammonium chloride. The resulting mixture was diluted with water and diethyl ether. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexane, 10/90 to 20/80) to give 0.56 g (62% yield) of 1-benzenesulfonyl-5-[2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-ethyl]-1H-indole-2-carbonitrile CCLXIX.

Workup

  1. stirringThe resulting mixture was stirred at −78° C. for 1.5 hour and at 0° C. for 1.5 hours
  2. customThe reaction was then quenched by addition of a saturated aqueous solution of ammonium chloride
  3. additionThe resulting mixture was diluted with water and diethyl ether
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe crude residue was purified by flash chromatography (EtOAc/hexane, 10/90 to 20/80)

Sources & evidence

ORD record
ord-08c9e295d21a4dc59c16678388beb837
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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