Methanol → 2-[(Tert-butyldimethylsilanyl)ethynyl]-5-(4-chlorophenyl)-3-fluoropyridine

HRID 734799Notes

Reaction equation

HRID 734799 reaction equation
CO.C(=O)([O-])[O-].[Na+].[Na+].Br[C:10]1[CH:11]=[C:12]([F:25])[C:13]([C:16]#[C:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[N:14][CH:15]=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30](OB(O)O)=[CH:29][CH:28]=1>O1CCOCC1>[Si:18]([C:17]#[C:16][C:13]1[C:12]([F:25])=[CH:11][C:10]([C:30]2[CH:31]=[CH:32][C:27]([Cl:26])=[CH:28][CH:29]=2)=[CH:15][N:14]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 17810664p-Chlorophenylboric acidHCID 690610065-Bromo-2-[(tert-butyldimethylsilanyl)ethynyl]-3-fluoropyridine

Product 1

HCID 690583282-[(Tert-butyldimethylsilanyl)ethynyl]-5-(4-chlorophenyl)-3-fluoropyridine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

10 mL of MeOH, 10 mL of 2N aqueous sodium carbonate solution, and 94 mg (0.13 mmol) of [1,1′-bis(diphenylphosphine)ferrocene]palladium (II) chloride were added to a solution of 1.61 g (5.14 mmol) of 5-bromo-2-[(tert-butyldimethylsilanyl)ethynyl]-3-fluoropyridine and 0.90 g (5.65 mmol) of 4-chlorophenylboric acid in 30 mL of 1,4-dioxane and the mixture was refluxed for 15 minutes. The reaction mixture was evaporated down in vacuo and diluted with EtOAc. The organic phase was washed with water and semisaturated aqueous sodium bicarbonate solution, dried over sodium sulfate, and evaporated down in vacuo. The residue was purified by column chromatography (silica gel, PE/DCM 1:1). Yield: 1.25 g (70% of theoretical); C19H21ClFNSi (M=345.913); calc.: molpeak (M+H)+: 346/348 (Cl); found: molpeak (M+H)+: 346/348 (Cl); HPLC-MS: 8.83 minutes (method B).

Workup

  1. temperaturethe mixture was refluxed for 15 minutes
  2. customThe reaction mixture was evaporated down in vacuo
  3. additiondiluted with EtOAc
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated down in vacuo
  7. customThe residue was purified by column chromatography (silica gel, PE/DCM 1:1)
  8. custom8.83 minutes (method B)

Sources & evidence

ORD record
ord-f58374b6bcb54c7681e42bd53480a572
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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