(5-Chloro-2-vinylpyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanone → 3-chloro-6-fluoro-7-methoxy-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

HRID 222318Notes

Reaction equation

HRID 222318 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]([C:12]2[C:17]([CH:18]=[CH2:19])=[CH:16][CH:15]=[C:14]([O:20][CH3:21])[C:13]=2[F:22])=[O:11])[C:5](C=C)=[N:6][CH:7]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10](=[O:11])[C:12]3[C:13]([F:22])=[C:14]([O:20][CH3:21])[CH:15]=[CH:16][C:17]=3[CH:18]=[CH:19][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 1

HCID 57722878(5-Chloro-2-vinylpyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanone

Product 1

HCID 577228443-chloro-6-fluoro-7-methoxy-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of (5-chloro-2-vinylpyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanone (6.20 g, 19.5 mmol) in toluene (1 L) was added Zhan IB catalyst (2.0 g, 2.8 mmol). The reaction mixture was purged with N2 for 20 min, heated to reflux overnight, cooled to room temperature, concentrated, and purified by flash chromatography to afford the title compound. LRMS (ESI) calc'd for (C15H9ClFNO2) [M+H]+, 290.0; found 290.0.

Workup

  1. customThe reaction mixture was purged with N2 for 20 min
  2. temperatureheated
  3. temperatureto reflux overnight
  4. concentrationconcentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-aa4cdfebae9e475bb6032add654c04bf
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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