Hexane → HCID 67229703, compound

HRID 1515785Notes

Reaction equation

HRID 1515785 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.C([Li])CCC.CCCCCC.[O:30]1[C:34]2([CH2:38][CH2:37][CH:36]([CH2:39][CH:40]=[O:41])[CH2:35]2)[O:33][CH2:32][CH2:31]1>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:40]([OH:41])[CH2:39][CH:36]2[CH2:37][CH2:38][C:34]3([O:30][CH2:31][CH2:32][O:33]3)[CH2:35]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8520781-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineHCID 71302026HCID 71302026, compoundHCID 178418339Butyllithium

Product 1

HCID 67229703HCID 67229703, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a suspension of 1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine (4.2 g, 16 mmol) in dry tetrahydrofuran (100 mL) at −78° C. was added a solution of n-butyllithium in n-hexane (1.6 M, 15 mL, 24 mmol) dropwise. The mixture was stirred at −78° C. for 15 min and then treated with (1,4-dioxa-spiro[4.4]non-7-yl)-acetaldehyde (5 g, 29 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, 30% ethyl acetate/hexanes) afforded 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(1,4-dioxa-spiro[4.4]non-7-yl)-ethanol as a colorless oil (5.5 g, 74%): LC/MS m/e calcd for C22H24N2O5S [M+H]+ 429.51, observed 429.3.

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, 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bdeed46f3bca47e2bd1e42e41f0199fe
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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