Diisopropylamine → HCID 67229605, compound

HRID 1515849Notes

Reaction equation

HRID 1515849 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:9]=[C:10]2[CH:16]=[CH:15][N:14]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:11]2=[N:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].C([N-][CH:31]([CH3:33])[CH3:32])(C)C.[Li+].C([Li])C[CH2:37][CH3:38].CCCCCC.C(NC(C)C)(C)C.[CH:53]1([CH:58]=[O:59])CCCC1>O1CCCC1>[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:9]=[C:10]2[CH:16]=[C:15]([CH:58]([OH:59])[CH2:53][CH:32]3[CH2:31][CH2:33][CH2:38][CH2:37]3)[N:14]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:11]2=[N:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 6

HCID 7912DiisopropylamineHCID 8058HexaneHCID 70106CyclopentanecarbaldehydeHCID 2724682Lithium diisopropylamideHCID 67229343tert-butyl (1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)carbamateHCID 178418339Butyllithium

Product 1

HCID 67229605HCID 67229605, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a suspension of (1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-carbamic acid tert-butyl ester (3.48 g, 9.33 mmol) in dry tetrahydrofuran (100 mL) at −78° C. was added freshly prepared lithium diisopropylamide [prepared by adding 1.6 M n-butyllithium in n-hexane (17.5 mL, 28 mmol) to a 0° C. solution of diisopropylamine (2.83 g, 28 mmol) in dry tetrahydrofuran (40 mL)] dropwise. The mixture was stirred at −78° C. for 5 min and then treated with cyclopentanecarbaldehyde (1.57 g, 14 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, 25% ethyl acetate/hexanes) afforded [1-benzenesulfonyl-2-(2-cyclopentyl-1-hydroxy-ethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-carbamic acid tert-butyl ester as a white solid (0.57 g, 44%): LC/MS m/e calcd for C25H31N3O5S [M+H]+ 486.61, observed 486.0.

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 (2×100 mL)
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification by flash column chromatography (QingDao silica gel, 200-300 mesh, 25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-de37a852e0cf46aabc8f3cfbb0ea527f
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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