Allyltributylstannane → 5-Allyl-3-(1-boc-2-(s)-azetidinylmethoxy)pyridine

HRID 365901Notes

Reaction equation

HRID 365901 reaction equation
[C:1]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18](Br)[CH:19]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:21]([Sn](CCCC)(CCCC)CCCC)[CH:22]=[CH2:23]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:23]([C:18]1[CH:19]=[C:14]([O:13][CH2:12][C@@H:9]2[CH2:10][CH2:11][N:8]2[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH:15]=[N:16][CH:17]=1)[CH:22]=[CH2:21]

Participants

5

Reactant 2

HCID 90628AllyltributylstannaneHCID 10688713(S)-Tert-butyl 2-(((5-bromopyridin-3-YL)oxy)methyl)azetidine-1-carboxylate

Product 1

HCID 213451795-Allyl-3-(1-boc-2-(s)-azetidinylmethoxy)pyridineYield 30%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

3-(1-BOC-2-(S)-azetidinylmethoxy)-5-bromopyridine (0.95 g, 2.77 mmol) in toluene (10 mL) was added tetrakis(triphenylphosphine) palladium (100 mg) and allyltributyltin (1.72 mL, 5.54 mmol). The mixture was stirred and refluxed for two days. Solvent was evaporated and the residue was chromatographed (silica gel; hexane/EtOAc, 5:1 to 1:1) to afford an oil (250 mg, 30%): 1H NMR (CDCl3, 300 MHz) δ 1.42 (s, 9H), 2.22-2.42 (m, 2H), 3.37 (d, 2H, J=7.0 Hz), 3.87-3.92 (m, 2H), 4.16 (m, 1H), 4.30 (m, 1H), 4.50 (m, 1H), 5.07-5.17 (m, 2H), 5.9 (m, 1H), 7.07 (m, 1H), 8.08 (m, 1H), 8.19 (d, 1H, J=3.0 Hz); MS (CI/NH3) m/z 305 (M+H)+.

Workup

  1. temperaturerefluxed for two days
  2. customSolvent was evaporated
  3. customthe residue was chromatographed (silica gel; hexane/EtOAc, 5:1 to 1:1)

Sources & evidence

ORD record
ord-3e80b82025a54098871dcba359036998
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

Loading…