Potassium tert-butoxide → HCID 57908153, compound

HRID 1044016Notes

Reaction equation

HRID 1044016 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8]C(=O)OC(C)(C)C)=[C:4]([C:16]#[C:17][CH:18]2[CH2:21][CH2:20][CH2:19]2)[CH:3]=1.CC([O-])(C)C.[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:16]=[C:17]([CH:18]3[CH2:21][CH2:20][CH2:19]3)[NH:8][C:5]2=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 57908178HCID 57908178, compound

Product 1

HCID 57908153HCID 57908153, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To the solution of tert-butyl 6-chloro-4-(cyclobutylethynyl)pyridin-3-ylcarbamate (2.6 g, 8.5 mmol) in DMF (50 mL) was added t-BuOK (1.9 g, 16 mmol). The reaction mixture was stirred at 90° C. for 2 h. The mixture was diluted with water and extracted with dichloromethane (3×50 mL). The extract was washed with brine, dried, concentrated in vacuo and purified by chromatography on silica gel (5-10% ethyl acetate in petroleum ether as eluant) to afford the pure product of 5-chloro-2-cyclobutyl-1H-pyrrolo[2,3-c]pyridine (0.9 g, 53% yield). 1H NMR (300 MHz, CDCl3) δ: 8.66 (br, s, 1H), 8.45 (s, 1H), 7.44 (s 1H), 6.27 (s, 1H), 3.75-3.52 (m, 1H), 2.52-1.90 (m, 6H).

Workup

  1. extractionextracted with dichloromethane (3×50 mL)
  2. washThe extract was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography on silica gel (5-10% ethyl acetate in petroleum ether as eluant)

Sources & evidence

ORD record
ord-697bbccf932e40f1bee9cb21841505ed
Source dataset
uspto-grants-2013_10
Patent number
US08563573B2

Reaction notes

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