Ethyl Acetate → HCID 77230810, compound

HRID 409021Notes

Reaction equation

HRID 409021 reaction equation
[Br:1][C:2]1[S:14][C:5]2=[N:6][C:7]([Cl:13])=[C:8]([CH:10]([OH:12])[CH3:11])[CH:9]=[C:4]2[CH:3]=1.C(OCC)(=O)C>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[S:14][C:5]2=[N:6][C:7]([Cl:13])=[C:8]([C:10](=[O:12])[CH3:11])[CH:9]=[C:4]2[CH:3]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 77230811HCID 77230811, compound

Product 1

HCID 77230810HCID 77230810, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A 2.2 g (7.5 mmol) portion of 1-(2-bromo-6-chlorothieno[2,3-b]pyridin-5-yl)-ethanol was dissolved in toluene and treated with manganese dioxide (6.5 g, 75 mmol, 10 eq). The mixture was heated to 90° C. overnight, then cooled rt and filtered through Celite™. The filter cake was rinsed with toluene and concentrated to afford crude material. The residue was purifed by column chromatography using ethyl acetate in hexanes to afford 1-(2-bromo-6-chlorothieno[2,3-b]pyridin-5-yl)ethanone. LC/MS (M+1, found=291.9). 1H NMR (400 MHz, CDCl3) δ 8.17 (s, 1H), 7.36 (s, 1H), 2.75 (s, 3H) ppm.

Workup

  1. temperaturecooled rt
  2. filtrationfiltered through Celite™
  3. washThe filter cake was rinsed with toluene
  4. concentrationconcentrated
  5. customto afford crude material

Sources & evidence

ORD record
ord-40f329f3b22644b090c90ae9f6192730
Source dataset
uspto-grants-2014_06
Patent number
US08759371B2

Reaction notes

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