Ethanol → 3-ethoxy-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 2196706Notes

Reaction equation

HRID 2196706 reaction equation
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13](=[O:20])[CH2:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH2:21](O)[CH3:22]>S(=O)(=O)(O)O.CCOC(C)=O>[CH2:21]([O:20][C:13]1[C:14]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[N:11]([S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])[CH:12]=1)[CH3:22]

Participants

5

Reactant 2

HCID 702EthanolHCID 67155645HCID 67155645, compound

Product 1

HCID 671559613-ethoxy-1-tosyl-1H-pyrrolo[2,3-b]pyridineYield 49%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-Tosyl-1H-pyrrolo[2,3-b]pyridin-3(2H)-one (234 mg, 0.815 mmol) was dissolved in ethanol (8 mL). A few drops of concentrated sulfuric acid were added, and the mixture was heated at reflux for 5 hours. The mixture was then allowed to cool to room temperature. The mixture was then diluted with EtOAc, washed with saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated. Flash 40 Biotage (40S cartridge, DCM) afforded 3-ethoxy-1-tosyl-1H-pyrrolo[2,3-b]pyridine (126 mg, 49%). 1H NMR (400 MHz, CDCl3) δ 8.42-8.45 m, 1H), 7.95-7.99 (m, 2H), 7.83-7.87 (m, 1H), 7.20-7.25 (m, 2H), 7.11-7.17 (m, 1H), 7.06 (s, 1H), 4.03-4.11 (m, 2H), 2.34 (s, 3H), 1.45-1.50 (m, 3H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 5 hours
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-38966fc13bdc41249908211f3eb1d37f
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

Loading…