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

HRID 1515683Notes

Reaction equation

HRID 1515683 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([CH2:19][O: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]([CH2:19][O: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:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 70106CyclopentanecarbaldehydeHCID 672296931-benzenesulfonyl-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridineHCID 178418339Butyllithium

Product 1

HCID 672293381-(1-benzenesulfonyl-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-cyclopentyl-ethanolYield 33.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a suspension of 1-benzenesulfonyl-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine (1.54 g, 5.1 mmol) in dry tetrahydrofuran (40 mL) at −78° C. was added n-butyllithium in n-hexane (1.6 M, 6.63 mmol, 4.14 mL) dropwise. The mixture was stirred at −78° C. for 5 min and then treated with cyclopentanecarbaldehyde (9.2 mmol, 1.03 g) dropwise. The resulting mixture was stirred at −78° C. for 1 h and quenched with brine. The mixture was extracted with ethyl acetate (2×200 mL), 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, 25% ethyl acetate/hexanes) afforded 1-(1-benzenesulfonyl-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-cyclopentyl-ethanol as a light yellow solid (710 mg, 33.6%): LC/MS m/e calcd for C22H26N2O4S [M+H]+ 415.53, observed 415.0.

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 (2×200 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1c95ff941c744824b615451fd93d9496
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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