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

HRID 1013732Notes

Reaction equation

HRID 1013732 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-d9ffdb446c18444d8096981d28b3e5b0
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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