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

HRID 2305114
Notes
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Reaction equation

HRID 2305114 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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) δ 1.38 (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-f9d2d426c9cf4db8a6f173f986c426eb
Source dataset
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06437138B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes