Hexane → 1-(1-benzenesulfonyl-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol

HRID 1515903Notes

Reaction equation

HRID 1515903 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([S:19][CH2:20][CH3:21])[CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:22]([Li])[CH2:23][CH2:24][CH3:25].[CH3:27][CH2:28][CH2:29]CCC.C1(C=[O:39])CCCC1>O1CCCC1>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([S:19][CH2:20][CH3:21])[CH:18]=[C:13]3[CH:12]=[C:11]2[CH:22]([OH:39])[CH2:23][CH:24]2[CH2:25][CH2:29][CH2:28][CH2:27]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 70106CyclopentanecarbaldehydeHCID 672294751-benzenesulfonyl-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridineHCID 178418339Butyllithium

Product 1

HCID 672276411-(1-benzenesulfonyl-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanolYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a suspension of 1-benzenesulfonyl-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine (2.68 g, 8.43 mmol) in dry tetrahydrofuran (60 mL) at −78° C. was added a solution of n-butyllithium in n-hexane (1.6M, 6.85 mL, 10.96 mmol) dropwise. The mixture was stirred at −78° C. for 10 min and then treated with cyclopentanecarbaldehyde (1.42 g, 12.65 mmol) dropwise. The resulting mixture was stirred at −78° C. for 1 h and quenched with brine. The mixture was extracted with ethyl acetate (2×100 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash column chromatography (silica gel from QingDao, 200-300 mesh, 20% ethyl acetate/hexanes) afforded 1-(1-benzenesulfonyl-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol (3.0 g, 83%) as a white solid: LC/MS m/e calcd for C22H26N2O3S2 [M+H]+ 431.59, observed 431.1.

Workup

  1. stirringThe resulting mixture was stirred at −78° C. for 1 h
  2. customquenched with brine
  3. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography (silica gel from QingDao, 200-300 mesh, 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4532637f16c84f3ca80341ea8c807c1a
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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