Reaction #452986

Reaction equation

5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-pyridine

sodium carbonate

1-naphthaleneboronic acid

sodium bicarbonate

→

oil

Yield 62.0%

5-(1-Naphthalenyl)-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine

Yield 62.0%

Solvents

benzene

Water

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was refluxed overnight
2. 2
   ExtractionThe mixture was extracted with EtOAc, which
3. 3
   Dryingwas dried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   OtherThe residue was chromatographed on a silica gel column
7. 7
   Washeluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90

Procedure

To a solution of 5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-pyridine (272 mg, 1.00 mmol) in benzene (2.0 mL) were added aqueous sodium carbonate (2.0M, 1.0 mL), tetrakis(triphenylphosphine)palladium(0) (35 mg, 0.03 mmol) and 1-naphthaleneboronic acid (189 mg, 1.10 mmol). The reaction mixture was refluxed overnight, then cooled to room temperature. Water (2 mL) was added, and solid sodium bicarbonate was added until the aqueous layer was saturated. The mixture was extracted with EtOAc, which was dried over MgSO4, filtered and concentrated. The residue was chromatographed on a silica gel column, eluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90 to afford a light yellowish oil (196 mg, 62%). MS (CI/NH3) m/z 319 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 1.71-1.92 (m, 3H), 2.00-2.10 (m, 1H), 2.27-2.38 (m, 1H), 2.51 (s, 3H), 2.66-2.75 (m, 1H), 3.09-3.17 (m, 1H), 3.98-4.14 (m, 2H), 7.34-7.57 (m, 5H), 7.72-7.96 (m, 3H),8.36-8.43 (m, 1H).

Source