Cesium carbonate → 1-Boc-3-((6-bromopyridin-3-YL)oxy)azetidine

HRID 2069725Notes

Reaction equation

HRID 2069725 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:19][CH:18](I)[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[C:9]([O:13][C:14]([N:16]1[CH2:19][CH:18]([O:8][C:5]2[CH:6]=[N:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27628652-Bromo-5-hydroxypyridineHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylate

Product 1

HCID 594737911-Boc-3-((6-bromopyridin-3-YL)oxy)azetidineYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

In a 250 mL round bottom flask, added 6-Bromo-pyridin-3-ol (4.69 g, 26.95 mmol) and 3-Iodo-azetidine-1-carboxylic acid tert-butyl ester (7.63g, 26.95 mmol) and Cs2CO3 (12.26 g, 37.73 mmol) in DMF (10 mL) with stirring under argon. The reaction was heated at 90° C. overnight. Reaction was then poured onto water (200 mL). The crude product was extracted with EtOAc (3×50 mL). The organic extraction was concentrated and purified by flash chromatography with 10% EtOAc in Hexanes to afford product 2.62 g (yield 30%) of 3-(6-Bromo-pyridin-3-yloxy)-azetidine-1-carboxylic acid tert-butyl ester as light brown solid.

Workup

  1. customReaction
  2. additionwas then poured onto water (200 mL)
  3. extractionThe crude product was extracted with EtOAc (3×50 mL)
  4. extractionThe organic extraction
  5. concentrationwas concentrated
  6. custompurified by flash chromatography with 10% EtOAc in Hexanes

Sources & evidence

ORD record
ord-85b2e1bd99de40dc997181f265b60ffb
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

Loading…