Diisopropylamine → HCID 67228984, compound

HRID 1515627Notes

Reaction equation

HRID 1515627 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([O:19][CH3:20])[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.C([N-][CH:25]([CH3:27])[CH3:26])(C)C.[Li+].C([Li])C[CH2:31][CH3:32].CCCCCC.C(NC(C)C)(C)C.[CH:47]1([CH:52]=[O:53])CCCC1>O1CCCC1>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=[C:13]3[CH:12]=[C:11]2[CH:52]([OH:53])[CH2:47][CH:26]2[CH2:25][CH2:27][CH2:32][CH2:31]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 6

HCID 7912DiisopropylamineHCID 8058HexaneHCID 70106CyclopentanecarbaldehydeHCID 2724682Lithium diisopropylamideHCID 222736501H-Pyrrolo[2,3-B]pyridine, 5-methoxy-1-(phenylsulfonyl)-HCID 178418339Butyllithium

Product 1

HCID 67228984HCID 67228984, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridine (prepared as in Example 10, 2.5 g, 8.68 mmol) in dry tetrahydrofuran (40 mL) at −78° C. was added freshly prepared lithium diisopropylamide [prepared by adding 1.6 M n-butyllithium in n-hexane (8.13 mL, 13.0 mmol) to a 0° C. solution of diisopropylamine (13.7 mmol, 1.96 mL) in dry tetrahydrofuran (20 mL)] dropwise. The mixture was stirred at −78° C. for 5 min and then cyclopentanecarbaldehyde (13.0 mmol, 1.46 g) was added 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, 20% ethyl acetate/hexanes) afforded 1-(-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-cyclopentyl-ethanol (2.3 g, 68%) as a white solid: LC/MS m/e calcd for C21H24N2O4S [M+H]+ 401.50, observed 401.0.

Workup

  1. customprepared
  2. stirringThe resulting mixture was stirred at −78° C. for 1 h
  3. customquenched with brine
  4. extractionThe mixture was extracted with ethyl acetate (2×200 mL)
  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-ac85533f39704772a0eee368790a4b3a
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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