2-Bromo-6-(tert-butyldiphenylsiloxy)methylpyridine → 2-(tert-Butyldiphenylsiloxy)methyl-6-phenylpyridine

HRID 1901115Notes

Reaction equation

HRID 1901115 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>C([O-])([O-])=O.[Na+].[Na+].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:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=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

5

Reactant 1

HCID 233702372-Bromo-6-(tert-butyldiphenylsiloxy)methylpyridine

Product 1

HCID 233701892-(tert-Butyldiphenylsiloxy)methyl-6-phenylpyridine

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 2-bromo-6-(tert-butyldiphenylsiloxy)methylpyridine (1 g; WO 94/00444), benzeneboric acid (400 mg) and tetrakis (triphenylphosphine) palladium (200 mg) in 2M Na2CO3 (25 mL) and THF (100 mL) was refluxed for 16 h. The THF was evaporated and the residue was extracted with EtOAc. The organics were dried (MgSO4), concentrated and chromatographed (silica gel; hexane/ethyl acetate (20:1)) to provide the title compound as a solid.

Workup

  1. temperaturewas refluxed for 16 h
  2. customThe THF was evaporated
  3. extractionthe residue was extracted with EtOAc
  4. dry with materialThe organics were dried (MgSO4)
  5. concentrationconcentrated
  6. customchromatographed (silica gel; hexane/ethyl acetate (20:1))

Sources & evidence

ORD record
ord-e5f5177229264eea963b84c8f8cd9fe6
Source dataset
uspto-grants-1996_11
Patent number
US05576338

Reaction notes

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