Ethyl Acetate → HCID 90008255, compound

HRID 590620Notes

Reaction equation

[C:1]([N:8]1[CH2:11][CH:10]([OH:12])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].[Br:15][C:16]1[CH:17]=[CH:18][C:19](I)=[N:20][CH:21]=1.CCOC(C)=O>CN(C=O)C>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([O:12][CH:10]2[CH2:11][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]2)=[N:20][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1-Boc-3-hydroxyazetidine (4.0 g, 23 mmol) was dissolved in DMF (30 mL) and cooled to 0° C. To this was added NaH (60% suspension, 0.83 g, 34 mmol) and it was stirred for 15 min. Finally, a solution of 5-bromo-2-iodopyridine (6.5 g, 23 mmol) in DMF (20 mL) was added to it and the reaction mixture was stirred at 70° C. for 5 h. It was, then, cooled to room temperature and diluted using EtOAc (200 mL). The organic layer was washed with water (150 mL×2), brine (150 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (10% EtOAc in hexane) to provide Va-2-I (4.5 g, 59% yield). LCMS: m/z; 329.

Workup

stirringthe reaction mixture was stirred at 70° C. for 5 h
temperaturecooled to room temperature
additiondiluted
washThe organic layer was washed with water (150 mL×2), brine (150 mL)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue obtained
customwas purified by silica gel column chromatography (10% EtOAc in hexane)

Sources & evidence

ORD record: ord-e70f23d523f142a2ae63207054211420
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233983B2

Reaction notes

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