Toluene → HCID 58687967, compound

HRID 746418Notes

Reaction equation

HRID 746418 reaction equation
Br[C:2]1[C:3]([O:21][CH3:22])=[N:4][C:5]([C:17]([F:20])([F:19])[F:18])=[CH:6][C:7]=1[CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].[C:23]1(C)[CH:28]=CC=C[CH:24]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:28]([C:2]1[C:3]([O:21][CH3:22])=[N:4][C:5]([C:17]([F:20])([F:19])[F:18])=[CH:6][C:7]=1[CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH:23]=[CH2:24]

Participants

4

Reactant 2

HCID 1140TolueneHCID 58687939HCID 58687939, compound

Product 1

HCID 58687967HCID 58687967, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of 3-bromo-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methoxy-6-(trifluoromethyl)pyridine (2.51 g, 6.27 mmol), allytributyltin (2.92 mL, 9.41 mmol), tetrakis(triphenylphosphine)palladium(0) (750 mg, 0.627 mmol) and toluene (15 mL) was flushed with nitrogen several times. The reaction mixture was stirred at reflux overnight. The reaction was filtered and concentrated under vacuum. The residue was purified by column chromatography (silica gel, 100% hexane to 5% EtOAc/hexane) to yield 3-allyl-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methoxy-6-(trifluoromethyl)pyridine (2.62 g, 100%). 1H-NMR (400 MHz, CDCl3) δ 7.55 (s, 1H), 5.85 (m, 1H), 4.93-5.11 (m, 2H), 4.74 (s, 2H), 4.04 (s, 3H), 3.37 (d, J=5Hz, 2H), 0.99 (s, 9H), 0.17 (s, 6H).

Workup

  1. customwas flushed with nitrogen several times
  2. temperatureat reflux overnight
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography (silica gel, 100% hexane to 5% EtOAc/hexane)

Sources & evidence

ORD record
ord-3f217b148cd04297b893f031fcf75dd6
Source dataset
uspto-grants-2008_07
Patent number
US07393844B2

Reaction notes

Loading…