Sodium Carbonate → 5-Phenyl-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine

HRID 365832Notes

Reaction equation

HRID 365832 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]2[CH2:13][CH2:12][N:11]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:5]=[N:6][CH:7]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[C:21]1([C:2]2[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]3[CH2:13][CH2:12][N:11]3[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:5]=[N:6][CH:7]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 10688713(S)-Tert-butyl 2-(((5-bromopyridin-3-YL)oxy)methyl)azetidine-1-carboxylate

Product 1

HCID 228726835-Phenyl-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridineYield 136.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 5-bromo-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine from Example 54b (1.03 g, 3 mmol), phenylboronic acid (920 mg, 7.5 mmol), Pd(0) (100 mg) and Na2CO3 (4 mL of a 2 M solution) were mixed in 20 mL of toluene, and the mixture was stirred at reflux for 3 hours. The solvent was removed under vacuum, and the residue was purified by chromatography on silica gel, eluting with CHCl3 :MeOH 100:2, to afford 1.39 g of the title compound. MS (CI/NH3) m/z 341 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.38 (s, 9H), 2.32 (m, 2H), 3.89 (m, 2H), 4.21 (m, 1H), 4.41 (m, 1H), 4.54 (m, 1H), 7.40 (m, 3H), 7.50 (m, 2H), 8.10 (m, 1H), 8.54 (m, 1H), 8.20 (m, 1H).

Workup

  1. temperatureat reflux for 3 hours
  2. customThe solvent was removed under vacuum
  3. customthe residue was purified by chromatography on silica gel
  4. washeluting with CHCl3 :MeOH 100:2

Sources & evidence

ORD record
ord-e4d5948e055f4fb494e0e931a083171e
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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