1-(5-Bromopyridin-2-yl)-1-(2,6-difluorophenyl)but-3-yn-2-one → 7-bromo-1-(2,6-difluorophenyl)-2H-quinolizin-2-one

HRID 1454978Notes

Reaction equation

HRID 1454978 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=2[F:20])[C:9](=[O:12])[C:10]#[CH:11])=[N:6][CH:7]=1>CN(CCN(C)C)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:11]=[CH:10][C:9](=[O:12])[C:8]=2[C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=2[F:20])[CH:7]=1

Participants

3

Reactant 1

HCID 575312431-(5-Bromopyridin-2-yl)-1-(2,6-difluorophenyl)but-3-yn-2-one

Product 1

HCID 575312307-bromo-1-(2,6-difluorophenyl)-2H-quinolizin-2-one

Reagents, catalysts & solvents 1

HCID 8037N,N,N',N'-TetramethylethylenediamineSolvent

Procedure

To a solution of 1-(5-bromopyridin-2-yl)-1-(2,6-difluorophenyl)but-3-yn-2-one (2 g) in TMEDA was heated to 90° C. for 1 h. LCMS analysis revealed the reaction was complete and the reaction was concentrated. The crude material was purified by silica gel chromatography (CH2Cl2/acetone) to yield the title compound.

Workup

  1. concentrationthe reaction was concentrated
  2. customThe crude material was purified by silica gel chromatography (CH2Cl2/acetone)

Sources & evidence

ORD record
ord-8d9dfddc5c6b42f5ba3a68dc4f89ac36
Source dataset
uspto-grants-2009_01
Patent number
US07482345B2

Reaction notes

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