Cesium carbonate → 3-(3-Ethynylphenyl)-2-fluoropyridine

HRID 646223Notes

Reaction equation

HRID 646223 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[C:15][Si](C)(C)C)[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CO.C(Cl)Cl.C(Cl)Cl>[C:14]([C:10]1[CH:9]=[C:8]([C:7]2[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=2)[CH:13]=[CH:12][CH:11]=1)#[CH:15]

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 687015872-Fluoro-3-{3-[(trimethylsilyl)ethynyl]phenyl}pyridine

Product 1

HCID 597726503-(3-Ethynylphenyl)-2-fluoropyridineYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 2-fluoro-3-{3-[(trimethylsilyl)ethynyl]phenyl}pyridine (2.20 g, 8.1 mmol) in MeOH/CH2Cl2 (1/1, 60 mL) is added Cs2CO3 (3.17 g, 9.7 mmol) at room temperature. After stirring for 1 h, the reaction mixture is diluted with CH2Cl2 and passed through a thin layer of silica gel. The solution is concentrated and the crude material is purified by chromatography (silica gel, EtOAc/hexane:20/80) to give the title compound (1.23 g, 77%) as a solid. mp: 45-47° C. MS (+) EI: 198 M+.

Workup

  1. concentrationThe solution is concentrated
  2. customthe crude material is purified by chromatography (silica gel, EtOAc/hexane:20/80)

Sources & evidence

ORD record
ord-85b76771f3904926a966dedd7beb3a6b
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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