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

HRID 2305110Notes

Reaction equation

HRID 2305110 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 mrL), and the mixture was heated at reflux for 16 hours. NaHCO3 solution (2%, lmL) was added, and the mixture was extracted with CHCl3. The CHCl3 was removed under reduced pressure, and the residue was chromatographed on a silica gel column, eluting with EtOAc/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 CHCl3
  4. customThe CHCl3 was removed under reduced pressure
  5. customthe residue was chromatographed on a silica gel column
  6. washeluting with EtOAc/hexane 1:1

Sources & evidence

ORD record
ord-97c8cf5ee7474ffb856a24a5762b7524
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

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