Water → 1-(3-Bromo-thieno[2,3-c]pyridin-5-yl)-ethanone

HRID 1394636Notes

Reaction equation

HRID 1394636 reaction equation
C(=O)(O)[O-].[Na+].O.[S:7]1[C:11]2=[CH:12][N:13]=[C:14]([C:16](=[O:18])[CH3:17])[CH:15]=[C:10]2[CH:9]=[CH:8]1.[Br:19]Br>C(Cl)(Cl)(Cl)Cl>[Br:19][C:9]1[C:10]2[C:11](=[CH:12][N:13]=[C:14]([C:16](=[O:18])[CH3:17])[CH:15]=2)[S:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 516892Sodium BicarbonateHCID 17952717HCID 17952717, compound

Product 1

HCID 179527371-(3-Bromo-thieno[2,3-c]pyridin-5-yl)-ethanoneYield 36%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

An aqueous saturated sodium bicarbonate solution (10 ml) and water (10 ml) was added to a solution of 1-thieno[2,3-c]pyridin-5-yl-ethanone (600 mg, 3.39 mmol) in carbon tetrachloride (5 ml). Bromine (0.523 ml, 10.2 mmol) was added and the reaction was stirred overnight. The biphasic mixture was allowed to separate and the organic layer was diluted with dichloromethane (25 ml) and washed with 10% sodium sulfide (in ammonium hydroxide) (1×20 mL), and brine (1×20 mL). The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was then purified by chromatography (chromatotron, 4μ plate, 0-200% ethyl acetate in hexanes) to yield 1-(3-bromo-thieno[2,3-c]pyridin-5-yl)-ethanone as a white solid (311.3 mg, 36%). 1H NMR (250 MHz, CDCl3): δ 9.20 (s, 1H), 8.54 (s, 1H), 7.30 (s, 1H), 7.30 (s, 1H), 2.85 (s, 3H). MS [E+] 255 & 257 (M+H)+.

Workup

  1. customto separate
  2. additionthe organic layer was diluted with dichloromethane (25 ml)
  3. washwashed with 10% sodium sulfide (in ammonium hydroxide) (1×20 mL), and brine (1×20 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was then purified by chromatography (chromatotron, 4μ plate, 0-200% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-da63371fc6814a6bb15a4643fa485d81
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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