Water → HCID 69658837, compound

HRID 2212979Notes

Reaction equation

HRID 2212979 reaction equation
O.[OH-].[Na+].[O:4]=[C:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=2)[N:13](S(C2C=CC(C)=CC=2)(=O)=O)[CH:12]=1>C1COCC1.C(OCC)(=O)C>[O:4]=[C:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[CH:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=2)[NH:13][CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21955938HCID 21955938, compound

Product 1

HCID 69658837HCID 69658837, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Water (50 mL) and sodium hydroxide (50 mL, 10 N) were added to a solution of 3-(2-oxo-cyclopentylmethyl)-1-(toluene-4-sulfonyl)-1H-indole-5-carbonitrile (1.0 g, 2.56 mMol) in THF (200 mL), and the mixture was stirred for 16 h. The reaction was diluted with ethyl acetate (300 mL), quenched with 1N HCl (100 mL), and then poured into a mixture of saturated aqueous sodium bicarbonate (200 mL) and brine (100 mL). The aqueous layer was extracted with ethyl acetate (4×250 mL). The combined organic layers were washed with brine (150 mL), dried over Na2SO4, and concentrated in vacuo. The crude material was purified by silica gel chromatography using a step gradient of 20% ethyl acetate/hexanes-85% ethyl acetate/hexanes to give 3-(2-oxo-cyclopentylidenemethyl)-1H-indole-5-carbonitrile as a yellow solid (400 mg, 67%) after drying under vacuum. 1H NMR (400 MHz, DMSO-d6) δ 8.43 (1H, s), 7.96 (1H, m), 7.63 (2H, m), 7.55 (1H, m), 2.85 (2H, m), 2.35 (2H, m), 2.00 (2H, m); LCMS (4.6×50 mm XTERRA C-18 S5 column, 5 mL/min, 0–100% MeOH/H2O/0.1% TFA, 2 min gradient): Tr=1.50 min, m/e 237 (M+H)+.

Workup

  1. customquenched with 1N HCl (100 mL)
  2. additionpoured into a mixture of saturated aqueous sodium bicarbonate (200 mL) and brine (100 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (4×250 mL)
  4. washThe combined organic layers were washed with brine (150 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b5433e25ea3f4d2fb58d912e6af5fba2
Source dataset
uspto-grants-2006_09
Patent number
US07105516B2

Reaction notes

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