Potassium Hydroxide → 1-(2-methoxyethyl)-7-(4-nitrophenylthio)-1H-pyrrolo[3,2-b]pyridine

HRID 1042872Notes

Reaction equation

HRID 1042872 reaction equation
[OH-].[K+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[CH:19]=[CH:20][NH:21][C:14]=23)=[CH:8][CH:7]=1)([O-:5])=[O:4].Br[CH2:23][CH2:24][O:25][CH3:26].BrOBr>O.CS(C)=O>[CH3:26][O:25][CH2:24][CH2:23][N:21]1[C:14]2[C:15](=[N:16][CH:17]=[CH:18][C:13]=2[S:12][C:9]2[CH:10]=[CH:11][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=2)[CH:19]=[CH:20]1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 809722-Bromoethyl methyl etherHCID 14513628Dibromine monoxideHCID 673182727-(4-nitrophenylthio)-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 673166791-(2-methoxyethyl)-7-(4-nitrophenylthio)-1H-pyrrolo[3,2-b]pyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A sealed vial was charged with potassium hydroxide (0.124 g, 2.21 mmol) and DMSO (5 mL). 7-(4-nitrophenylthio)-1H-pyrrolo[3,2-b]pyridine (0.150 g, 0.553 mmol) was added and the reaction was stirred for 45 minutes. 1-Bromo-2-methoxyethane (0.104 ml, 1.11 mmol) was added, the system was flushed with argon, and the reaction was stirred at RT for 2 hours. LC-MS indicated starting material remaining, so 1 eq. bromoether was added and the reaction stirred for two more hours. The reaction was diluted with water and extracted four times with DCM and twice with ethyl acetate. The combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (gradient elution 0-5% MeOH:DCM) to afford 1-(2-methoxyethyl)-7-(4-nitrophenylthio)-1H-pyrrolo[3,2-b]pyridine as an orange oil that solidified under high vacuum. MS: M+H+=330.1

Workup

  1. customthe system was flushed with argon
  2. stirringthe reaction was stirred at RT for 2 hours
  3. stirringthe reaction stirred for two more hours
  4. extractionextracted four times with DCM
  5. dry with materialThe combined organic layers were dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe material was purified via column chromatography (gradient elution 0-5% MeOH:DCM)

Sources & evidence

ORD record
ord-2998f1117b2840b28e99026de30f3d52
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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