Potassium tert-butoxide → 6,7,8,9-Tetrahydropyrido[2,3-b]indolizine

HRID 573282Notes

Reaction equation

HRID 573282 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[C:7][C:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][N:9]=1.CC([O-])(C)C.[K+]>CC#N.C1COCC1>[N:9]1[C:8]2[CH:7]=[C:6]3[N:14]([C:13]=2[CH:12]=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5]3

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 667276242-(6-Chlorohex-1-ynyl)pyridin-3-amine

Product 1

HCID 667277726,7,8,9-Tetrahydropyrido[2,3-b]indolizineYield 68.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(6-chlorohex-1-ynyl)pyridin-3-amine (300 mg) in CH3CN (3 ml) was added a solution of KOtBu (387 mg) in THF (3.5 mL) at 0.0° C. The mixture was stirred at 0° C. for 30 min. The mixture was quenched with water at 0° C. and extracted with AcOEt. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (170 mg).

Workup

  1. customThe mixture was quenched with water at 0° C.
  2. extractionextracted with AcOEt
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-246f11f2a0af4146902d2e9f4d9373ea
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

Loading…