Water → 3-bromo-5-methylthieno[3,2-c]pyridin-6(5H)-one

HRID 389546Notes

Reaction equation

HRID 389546 reaction equation
[Br:1][C:2]1[C:6]2=[CH:7][NH:8][C:9](=[O:11])[CH:10]=[C:5]2[S:4][CH:3]=1.[H-].[Na+].[CH3:14]I.O>CN(C=O)C>[Br:1][C:2]1[C:6]2=[CH:7][N:8]([CH3:14])[C:9](=[O:11])[CH:10]=[C:5]2[S:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 667597493-bromothieno[3,2-c]pyridin-6(5H)-one

Product 1

HCID 667612803-bromo-5-methylthieno[3,2-c]pyridin-6(5H)-oneYield 48.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-bromothieno[3,2-c]pyridin-6(5H)-one (235 mg, 1.02 mmol) in DMF (3.9 mL) was added sodium hydride (25.7 mg, 1.07 mmol). The mixture stirred 1 h at room temperature, and then methyl iodide (69.9 μL, 1.12 mmol) was added. The reaction stirred a further 1 h at room temperature and then was poured into water (100 mL). The mixture was extracted with dichloromethane (3×50 mL). The combined organic fractions were washed with water (3×50 mL), dried over sodium sulfate, filtered, and concentrated. Trituration with diethyl ether (˜5 mL) and filtration to collect the resultant solid afforded 120 mg (48%) of the title compound as a tan solid. 1H NMR (400 MHz, CDCl3): δ 7.84 (s, 1 H), 6.91 (s, 1 H), 6.89 (d, J=0.8 Hz, 1 H), 3.75 (s, 3 H); MS (ESI): 244.03, 245.98 [M+H]+; HPLC tR=2.76 min (ZQ3, polar—4 min).

Workup

  1. stirringThe reaction stirred a further 1 h at room temperature
  2. extractionThe mixture was extracted with dichloromethane (3×50 mL)
  3. washThe combined organic fractions were washed with water (3×50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationTrituration with diethyl ether (˜5 mL) and filtration
  8. customto collect the resultant solid

Sources & evidence

ORD record
ord-9162a9f9f4f2428db2cc0dcd5a0621a8
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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