Sodium hydride → 2-[3-(Azetidin-yl)propoxy]-5-bromopyridine

HRID 1486943Notes

Reaction equation

HRID 1486943 reaction equation
[H-].[Na+].[N:3]1([CH2:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4]1.[Br:11][C:12]1[CH:13]=[CH:14][C:15](F)=[N:16][CH:17]=1>C1COCC1>[N:3]1([CH2:7][CH2:8][CH2:9][O:10][C:15]2[CH:14]=[CH:13][C:12]([Br:11])=[CH:17][N:16]=2)[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27831685-Bromo-2-fluoropyridineHCID 204376893-(Azetidin-1-yl)propan-1-ol

Product 1

HCID 1184986242-[3-(Azetidin-yl)propoxy]-5-bromopyridineYield 122%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (1.364 g, 56.82 mmol) was added to 3-(azetidin-1-yl)propan-1-ol (2.62 g, 22.73 mmol) in THF (20 mL) at ambient temperature under an inert atmosphere and the reaction stirred for 10 minutes. 5-Bromo-2-fluoropyridine (2.0 g, 11.36 mmol) was added and the resulting solution stirred for 1 h before being quenched with water (20 mL) and extracted with EtOAc (5×50 mL). The organics were combined, dried over Na2SO4, filtered and concentrated in vacuo to afford the desired material (3.75 g, 122%) as a white solid. NMR Spectrum: 1H NMR (300 MHz, CDCl3) δ 1.80 (2H, m), 2.11 (2H, m), 2.55 (2H, t), 3.18 (4H, t), 4.328 (2H, t), 6.64 (1H, d), 7.62 (1H, dd), 8.16 (1H, d). Mass Spectrum: m/z (ES+)[M+H]+=271.

Workup

  1. stirringthe resulting solution stirred for 1 h
  2. custombefore being quenched with water (20 mL)
  3. extractionextracted with EtOAc (5×50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c149d05e5dc4d3a94d70c477ed97f60
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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