Cesium carbonate → HCID 86719114, compound

HRID 572933Notes

Reaction equation

HRID 572933 reaction equation
Br[C:2]1[N:7]=[C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:4][CH:3]=1.Cl.[NH:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1.N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.[Cu]I>[OH:18][CH:16]1[CH2:17][N:14]([C:2]2[N:7]=[C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:4][CH:3]=2)[CH2:15]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 145742L-ProlineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 71720999Methyl (6-bromopyridin-2-yl)acetate

Product 1

HCID 86719114HCID 86719114, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

The solution of methyl 2-(6-bromopyridin-2-yl)acetate (500.0 mg, 2.17 mmol), azetidin-3-ol hydrochloride (285.9 mg, 2.61 mmol), CuI (248.3 mg, 1.30 mmol), L-proline (149.7 mg, 1.30 mmol) and Cs2CO3 (24.7 g, 75.7 mmol) in DMSO (6 mL) was stirred at 90 degree for 12 h under N2. After cooling to room temperature, the reaction mixture was filtered, diluted with H2O and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by a standard method to give desired compound.

Workup

  1. filtrationthe reaction mixture was filtered
  2. additiondiluted with H2O
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by a standard method

Sources & evidence

ORD record
ord-a51bc4e7bdcb4e60965030f0abcfc71d
Source dataset
uspto-grants-2015_05
Patent number
US09029531B2

Reaction notes

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