Ammonium Chloride → 1-(5-Bromopyridin-2-yl)-1-(2,6-difluorophenyl)but-3-yn-2-one

HRID 1454977Notes

Reaction equation

HRID 1454977 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])[C:9](=[O:16])[C:10]#[C:11][Si](C)(C)C)=[N:6][CH:7]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])[C:9](=[O:16])[C:10]#[CH:11])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 575312421-(5-Bromopyridin-2-yl)-1-(2,6-difluorophenyl)-4-(trimethylsilyl)but-3-yn-2-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(5-bromopyridin-2-yl)-1-(2,6-difluorophenyl)-4-(trimethylsilyl)but-3-yn-2-one (4.1 g) in THF was added TBAF (12 mL, 1N in THF) at 0° C. After stirring at 0° C. for 15 min, the reaction was poured into aqueous NH4Cl, and extracted with EtOAc. The combined organic layers were washed with water, brine, dried over MgSO4, and concentrated to an oil. The crude product was purified by silica gel chromatography (CH2Cl2) to give the title compound.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to an oil
  5. customThe crude product was purified by silica gel chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-74d25f0984ba4acfb2b03f79512a2456
Source dataset
uspto-grants-2009_01
Patent number
US07482345B2

Reaction notes

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