HCID 67410607, compound → HCID 67412826, compound

HRID 222312Notes

Reaction equation

HRID 222312 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:12]([OH:13])[C:11]3[CH:14]=[C:15]([CH:18]([OH:22])[CH:19]([F:21])[F:20])[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1>C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15]([CH:18]([OH:22])[CH:19]([F:20])[F:21])[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 67410607HCID 67410607, compound

Product 1

HCID 67412826HCID 67412826, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Manganese dioxide (0.16 g, 1.9 mmol) was added to a solution of 3-chloro-7-(2,2-difluoro-1-hydroxyethyl)-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-ol (60 mg, 0.19 mmol) in ethyl acetate (2 mL) and the mixture was stirred at room temperature for 8 hours. The slurry was then filtered through celite, eluting with ethyl acetate. The filtrate was concentrated in vacuo, and purified via flash chromatography (silica, 0-50% ethyl acetate/hexanes) to afford the title compound. 1H NMR (600 MHz, CD3OD) δ 8.75 (d, 1H), 8.39 (d, 1H), 8.25 (d, 1H), 7.81 (dd, 1H), 7.65 (d, 1H), 7.29 (d, 1H), 7.19 (d, 1H), 5.89 (dt, 1H), 4.93 (dt, 1H). Hydroxyl proton was not observed.

Workup

  1. filtrationThe slurry was then filtered through celite
  2. washeluting with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified via flash chromatography (silica, 0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-543068122e57449abbb87f85eb7bc8c6
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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