Water → HCID 60248807, compound

HRID 1747818Notes

Reaction equation

HRID 1747818 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([OH:6])[CH2:3]1.Cl[C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[F:15][C:14]([F:17])([F:16])[C:13]1[C:8]([N:2]2[CH2:5][CH:4]([OH:6])[CH2:3]2)=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 5898332-Chloro-3-(trifluoromethyl)pyridineHCID 27592903-Hydroxyazetidine hydrochloride

Product 1

HCID 60248807HCID 60248807, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of azetidin-3-ol hydrochloride (500 mg), 2-chloro-3-(trifluoromethyl)pyridine (425 mg) and cesium carbonate (1.14 g) in DMF (5 ml) was stirred at 50° C. for 12 hr, and water was added. The reaction mixture was extracted with ethyl acetate, the extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (120 mg).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d7007b473b814c8e8b15186ac00748db
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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