Water → HCID 178503545, compound

HRID 1296803Notes

Reaction equation

HRID 1296803 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[S:15][C:14](=[S:16])[NH:13][C:12]2=[O:17])=[CH:2]1.IC.[CH3:20]CN(C(C)C)C(C)C.O>C(O)C>[CH3:20][S:16][C:14]1[S:15][C:11](=[CH:10][C:3]2[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:1][CH:2]=2)[C:12](=[O:17])[N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 178518565HCID 178518565, compound

Product 1

HCID 178503545HCID 178503545, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

The suspension of 5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-2-thioxo-thiazolidin-4-one (2.2 g, 8.22 mmol), iodomethane (1.05 mL, 16.8 mmol) and DIEA (3.0 mL, 16.8 mmol) in anhydrous ethanol (110 mL) was stirred at 100° C. for 2 h. After adding water (200 mL), the solid was collected by filtration, washed with water and dried to obtain 2-methylsulfanyl-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-thiazol-4-one (1.48 g, 60.8%) as a grey solid. LC-MS m/e 276 (MH+).

Workup

  1. filtrationthe solid was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-ef8b502b089046289565bc0d951ddb2e
Source dataset
uspto-grants-2007_07
Patent number
US07247727B2

Reaction notes

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