Sodium Hydroxide → 2-(1-(3-chloro-phenyl)-3-methyl-but-1-enyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1515936Notes

Reaction equation

HRID 1515936 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:13]2[N:21](S(C3C=CC=CC=3)(=O)=O)[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH:14]=2)=[CH:9][CH:10]([CH3:12])[CH3:11])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C(O)C.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:13]2[NH:21][C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH:14]=2)=[CH:9][CH:10]([CH3:12])[CH3:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 672296642-(1-(3-chloro-phenyl)-3-methyl-but-1-enyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 672292502-(1-(3-chloro-phenyl)-3-methyl-but-1-enyl)-1H-pyrrolo[2,3-b]pyridineYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 2-(1-(3-chloro-phenyl)-3-methyl-but-1-enyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (2.5 g, 5.7 mmol) in ethanol (45 mL) and tetrahydrofuran (90 mL) was treated with a 10% aqueous sodium hydroxide solution (15 mL). The reaction was stirred at 70° C. for 16 h. The solvent was removed in vacuo and the obtained precipitate was filtered and washed with water (3×50 mL) and ethyl acetate (20 mL) to afford 2-(1-(3-chloro-phenyl)-3-methyl-but-1-enyl)-1H-pyrrolo[2,3-b]pyridine (1.3 g, 77%) as a white solid: 1H NMR (300 MHz, d6-DMSO) δ ppm 11.57 (s, 1H), 8.17 (dd, 1H, J1=4.5 Hz, J2=1.5 Hz), 7.93 (dd, 1H, J1=8.4 Hz, J2=1.8 Hz), 7.31 (m, 2H), 7.21 (m, 1H), 7.15 (m, 1H), 7.05 (m, 1H), 6.40 (s, 1H), 6.21 (d, 1H, J=9.9 Hz), 2.57 (m, 1H), 1.03-1.01 (m, 6H).

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationthe obtained precipitate was filtered
  3. washwashed with water (3×50 mL) and ethyl acetate (20 mL)

Sources & evidence

ORD record
ord-fd54eecf7bf149289a3aa0fb93435f85
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

Loading…