2-Bromo-6-(tert-butyldiphenylsiloxy)methylpyridine → 2-(tert-Butyldiphenylsiloxy)methyl-6-(4-fluorophenyl)pyridine

HRID 1901117Notes

Reaction equation

HRID 1901117 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][O:9][Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1.[F:27][C:28]1[CH:33]=[CH:32][C:31]([Mg]Br)=[CH:30][CH:29]=1>CCOCC.C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:9]([CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:31]2[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=2)[N:3]=1)[Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 2

HCID 233702372-Bromo-6-(tert-butyldiphenylsiloxy)methylpyridineHCID 178418676HCID 178418676, compound

Product 1

HCID 233701832-(tert-Butyldiphenylsiloxy)methyl-6-(4-fluorophenyl)pyridine

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-bromo-6-(tert-butyldiphenylsiloxy)methylpyridine (1 g; WO 94/00444), 4-fluorophenylmagnesium bromide (3.5 mL of a 2M solution in Et2O) and tetrakis (triphenylphosphine) palladium (200 mg) in THF (20 mL) was refluxed for 4 h. To the mixture was added NH4OAc buffer and the mixture was extracted with EtOAc. The organics were dried (MgSO4), concentrated and chromatographed (silica gel; hexane/EtOAc (30:1)) to provide the title compound as an oil.

Workup

  1. temperaturewas refluxed for 4 h
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated
  5. customchromatographed (silica gel; hexane/EtOAc (30:1))

Sources & evidence

ORD record
ord-79187af6a1a34680acdd1d53a5bf3975
Source dataset
uspto-grants-1996_11
Patent number
US05576338

Reaction notes

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