HCID 12071331, compound → HCID 69979930, compound

HRID 2301972Notes

Reaction equation

HRID 2301972 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:16][CH2:17][C:18]#[CH:19])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:20][O:21][C:22](=[O:43])[CH2:23][CH:24]1[CH2:33][C:32]2[C:27](=[CH:28][C:29](OS(C(F)(F)F)(=O)=O)=[CH:30][CH:31]=2)[NH:26][C:25]1=[O:42].CCOC(C)=O.CCCCCC>CN1CCCC1.[Cu]I>[CH3:20][O:21][C:22](=[O:43])[CH2:23][CH:24]1[CH2:33][C:32]2[C:27](=[CH:28][C:29]([C:19]#[C:18][CH2:17][CH2:16][N:8]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:30][CH:31]=2)[NH:26][C:25]1=[O:42]

Participants

6

Reactant 3

HCID 12071331HCID 12071331, compoundHCID 21226206Ethyl acetate hexaneHCID 58908618HCID 58908618, compound

Product 1

HCID 69979930HCID 69979930, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 84541-MethylpyrrolidineSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of N-but-3-ynyl-imidodicarbonic acid di-tert-butyl ester (4.65 g, 17.3 mmol), [2-oxo-7-(trifluoro-methanesulfonyloxy)-1,2,3,4-tetrahydro-quinolin-3-yl]-acetic acid methyl ester (6.36 g, 17.3 mmol), tetrakis (triphenylphosphine)palladium (2.0 g, 1.7 mmol) and copper (I) iodide (0.49 g, 2.6 mmol) in N-methylpyrrolidine (50 mL; purged with N2) was heated to 60° C. The resulting solution was treated with the original amounts of both catalysts, two additional times, at 1.5 h intervals. After 22 h, the reaction mixture was filtered and concentrated. The resulting dark oil was treated with saturated aqueous NH4Cl (250 mL), extracted with chloroform (3×250 mL), dried (MgSO4) and concentrated to give a dark mixture of oil and foam (16.2 g). Flash chromatography (260 g silica; 5%, then 10%, then 20%, then 40% EtOAc-hexane) gave the title compound (5.2 g, 62% yield) as an impure yellow foam.

Workup

  1. additionThe resulting solution was treated with the original amounts of both catalysts, two additional times, at 1.5 h intervals
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. additionThe resulting dark oil was treated with saturated aqueous NH4Cl (250 mL)
  5. extractionextracted with chloroform (3×250 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give

Sources & evidence

ORD record
ord-350c6a9b3a0845a6a2638334ce17f79a
Source dataset
uspto-grants-2002_08
Patent number
US06429214B1

Reaction notes

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