Boric Acid → 5-phenyl-3-(1-tosyl-2-(S)-pyrrolidinylmethoxy)pyridine

HRID 1780324Notes

Reaction equation

HRID 1780324 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[S:15]([C:18]2[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:5]=[N:6][CH:7]=1.B(O)(O)O.C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[C:18]1([C:2]2[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]3[CH2:14][CH2:13][CH2:12][N:11]3[S:15]([C:18]3[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:5]=[N:6][CH:7]=2)[CH:24]=[CH:23][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7628Boric AcidHCID 516892Sodium BicarbonateHCID 541585905-bromo-3-(1-tosyl-2-(S)-pyrrolidinylmethoxy)pyridine

Product 1

HCID 539087355-phenyl-3-(1-tosyl-2-(S)-pyrrolidinylmethoxy)pyridineYield 13.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5-bromo-3-(1-tosyl-2-(S)-pyrrolidinylmethoxy)pyridine from step 51b (300 mg, 10.73 mmol), boric acid (107 mg, 10.88 mmol) and Pd(0) (26 mg) were mixed together in benzene (2 mL), and the mixture was heated at reflux for 16 hours. NaHCO3 solution (2%, 1 mL) was added, and the mixture was extracted with chloroform. The CHCl3 was removed under reduced pressure, and the residue was chromatographed on a silica gel column, eluting with ethyl acetate/hexane 1:1 to afford the title compound (300 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hours
  3. extractionthe mixture was extracted with chloroform
  4. customThe CHCl3 was removed under reduced pressure
  5. customthe residue was chromatographed on a silica gel column
  6. washeluting with ethyl acetate/hexane 1:1

Sources & evidence

ORD record
ord-eae125171f7245be8199721ad6c5a11e
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

Loading…