Hexane → HCID 67228830, compound

HRID 1515687Notes

Reaction equation

HRID 1515687 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][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.[CH2:19]([Li])[CH2:20][CH2:21][CH3:22].[CH3:24][CH2:25][CH2:26]CCC.C1(C=[O:36])CCCC1>O1CCCC1>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[CH:19]([OH:36])[CH2:20][CH:21]2[CH2:22][CH2:26][CH2:25][CH2:24]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 70106CyclopentanecarbaldehydeHCID 8520781-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineHCID 178418339Butyllithium

Product 1

HCID 67228830HCID 67228830, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a −78° C. suspension of 1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine (800.7 mg, 3.1 mmol) in dry tetrahydrofuran (40 mL) was added 1.6 M n-butyllithium in n-hexane (2.2 mL, 3.5 mmol) dropwise. The mixture was stirred at −78° C. for 5 min before adding cyclopentanecarbaldehyde (516 mg, 4.6 mmol) dropwise. The resulting mixture was stirred at −78° C. for 1 h and quenched by adding brine. The mixture was extracted with ethyl acetate (200 mL×2), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (20% ethyl acetate/hexanes) afforded 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol as colorless oil (690 mg, 60%): LC/MS m/e calcd for C20H23N2O3S [M+H]+ 371.14, observed 371.0.

Workup

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

Sources & evidence

ORD record
ord-bea8015854264857926d97ea6d9f7219
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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