3-Methylbutanal → HCID 67228631, compound

HRID 1515930Notes

Reaction equation

HRID 1515930 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([N-]C(C)C)(C)C.[Li+].[CH3:27][CH:28]([CH3:32])[CH2:29][CH:30]=[O:31]>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:30]([OH:31])[CH2:29][CH:28]([CH3:32])[CH3:27])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 115523-MethylbutanalHCID 8520781-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineHCID 2724682Lithium diisopropylamide

Product 1

HCID 67228631HCID 67228631, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a suspension of 1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine (5.0 g, 19.3 mmol) in dry tetrahydrofuran (125 mL) at −78° C. was added lithium diisopropylamide (14.5 mL, 29 mmol) dropwise. The mixture was stirred at −78° C. for 10 min and then treated with 3-methylbutanal (3.9 g, 45 mmol) dropwise. The resulting mixture was stirred at −78° C. for 1.5 h. At this time, the reaction was quenched with a saturated aqueous sodium chloride solution. The resulting mixture was then extracted with ethyl acetate (3×150 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Silica gel column chromatography (10-15% ethyl acetate/petroleum ether) afforded 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-methyl-butan-1-ol (3.4 g, 51.8%) as a white solid: 1H NMR (300 MHz, d6-DMSO): δ 8.29 (d, 1H, J=3.3 Hz), 8.10 (d, 2H, J=7.8 Hz), 7.96 (d, 1H, J=7.5 Hz), 7.72-7.59 (m, 3H), 7.28-7.24 (m, 1H), 6.81 (s, 1H), 5.55-5.46 (m, 2H), 2.05-1.90 (m, 1H), 1.81-1.73 (m, 1H), 1.04 (d, 3H, J=6.3 Hz), 0.97 (s, 3H), 0.95 (s, 3H).

Workup

  1. stirringThe resulting mixture was stirred at −78° C. for 1.5 h
  2. customAt this time, the reaction was quenched with a saturated aqueous sodium chloride solution
  3. extractionThe resulting mixture was then extracted with ethyl acetate (3×150 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-133fe775a54e4653a009b8d8d9d7168d
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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