Potassium Carbonate → HCID 117988321, compound

HRID 2206081Notes

Reaction equation

HRID 2206081 reaction equation
I[C:2]1[C:7]([C:8]([NH:10][NH:11][CH:12]2[CH2:16][CH2:15][O:14][CH2:13]2)=[O:9])=[C:6]([O:17][CH3:18])[N:5]=[CH:4][CH:3]=1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[CH3:18][O:17][C:6]1[C:7]2[C:8](=[O:9])[NH:10][N:11]([CH:12]3[CH2:16][CH2:15][O:14][CH2:13]3)[C:2]=2[CH:3]=[CH:4][N:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 117988314HCID 117988314, compound

Product 1

HCID 117988321HCID 117988321, compoundYield 32.2%

Reagents, catalysts & solvents 2

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

Procedure

A solution of 4-iodo-2-methoxy-N′-(tetrahydrofuran-3-yl)nicotinohydrazide (1.26 g), L-proline (0.080 g), potassium carbonate (0.957 g) and copper(I) iodide (0.066 g) in DMSO (25 mL) was stirred under nitrogen atmosphere at room temperature for 3 hr. The reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.263 g).

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a22f4f01306e4b44b5971a4cd76c6ba9
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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