Iodoethane → N-(Benzensulfonyl)-5-chloro-2-ethylindole

HRID 11397Notes

Reaction equation

HRID 11397 reaction equation
[Li][C:2](C)(C)[CH3:3].[C:6]1([S:12]([N:15]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[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.C(I)C>C1COCC1>[C:6]1([S:12]([N:15]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[CH:17]=[C:16]2[CH2:2][CH3:3])(=[O:14])=[O:13])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 64726505-Chloro-1-(phenylsulfonyl)indoleHCID 178418306HCID 178418306, compound

Product 1

HCID 21974278N-(Benzensulfonyl)-5-chloro-2-ethylindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

t-BuLi (3.7 mL of 1.7 M solution in pentane) was added dropwise to a solution of N-(benzensulfonyl)-5-chloroindole (1) (J. Org. Chem. 1981, 46, 3859) (1.5 g, 5.14 mmol) in THF (35 mL) at −70° C., under a nitrogen atmosphere. The mixture was stirred for 15 min, allowed to warm to room temperature over 20 min, cooled to −70° C., and treated with a solution of ethyl iodide (0.84 mL, 10.5 mmol) in dry THF (5 mL). The mixture was stirred at −78° C. for 1 h, allowed to warm to room temperature, stirred for 2 h, poured into ice (15 g), and a saturated aqueous NH4Cl solution and then extracted with ether (3×20 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo to give a residue which was purified by flash chromatography (silica gel, cyclohexane/ethyl acetate, 8:2) and crystallization from ethylacetate/cyclohexane.

Workup

  1. temperaturecooled to −70° C.
  2. stirringThe mixture was stirred at −78° C. for 1 h
  3. temperatureto warm to room temperature
  4. stirringstirred for 2 h
  5. extractiona saturated aqueous NH4Cl solution and then extracted with ether (3×20 mL)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo
  9. customto give a residue which
  10. customwas purified by flash chromatography (silica gel, cyclohexane/ethyl acetate, 8:2) and crystallization from ethylacetate/cyclohexane

Sources & evidence

ORD record
ord-25f95517642f49208b1291046c1ef585
Source dataset
uspto-grants-2006_08
Patent number
US07098233B2

Reaction notes

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