Hexane → HCID 67229040, compound

HRID 1515913Notes

Reaction equation

HRID 1515913 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[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.[CH2:23]([Li])[CH2:24][CH2:25][CH3:26].[CH3:28][CH2:29][CH2:30]CCC.C1(C=[O:40])CCCC1>O1CCCC1>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:18]=[C:13]3[CH:12]=[C:11]2[CH:23]([OH:40])[CH2:24][CH:25]2[CH2:26][CH2:30][CH2:29][CH2:28]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 70106CyclopentanecarbaldehydeHCID 67227783HCID 67227783, compoundHCID 178418339Butyllithium

Product 1

HCID 67229040HCID 67229040, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a suspension of 1-benzenesulfonyl-5-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine (1.0 g, 3.07 mmol) in dry tetrahydrofuran (50 mL) at −78° C. was added a solution of n-butyllithium in n-hexane (2.5 M, 1.5 mL, 3.68 mmol) dropwise. The mixture was stirred at −78° C. for 5 min and then treated with cyclopentanecarbaldehyde (0.52 g, 4.6 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 (QingDao silica gel, 200-300 mesh, 50% dichloromethane/hexanes) afforded 1-(1-benzenesulfonyl-5-trifluoromethyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol (1.34 g, 100%): LC/MS m/e calcd for C21H21F3N2O3S [M+H]+ 439.47, observed 438.7.

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 (QingDao silica gel, 200-300 mesh, 50% dichloromethane/hexanes)

Sources & evidence

ORD record
ord-f883f95771634c8fa13b05dbbd132317
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

Loading…