Triethylamine → 7-[3-(4-methoxycarbonyl-phenyl)-1-pentyl-prop-2-ynyl]-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 2415214Notes

Reaction equation

HRID 2415214 reaction equation
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:19]([O:23][C:24]([N:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([CH:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:37]#[CH:38])[CH:34]=2)[C:29]([CH3:45])([CH3:44])[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>CN(C=O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:19]([O:23][C:24]([N:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([CH:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:37]#[C:38][C:2]3[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=3)[CH:34]=2)[C:29]([CH3:44])([CH3:45])[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 69273Methyl 4-iodobenzoateHCID 865890284,4-dimethyl-7-(1-pentyl-prop-2-ynyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

Product 1

HCID 692158867-[3-(4-methoxycarbonyl-phenyl)-1-pentyl-prop-2-ynyl]-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl esterYield 53.5%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 0.043 g of methyl 4-iodobenzoate, 0.093 mL of triethylamine, 4.6 mg of Pd(Ph3P)2Cl2 and 2.5 mg of copper (I) iodide in 2 ml of DMF was degassed and treated with a solution of 4,4-dimethyl-7-(1-pentyl-prop-2-ynyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (0.049 g, 0.13 mmole) in 1 mL of DMF. The reaction mixture was stirred at room temperature for 18 hours, diluted with 10 mL of water and extracted with three 10 mL portions of ethyl acetate. The combined organic extracts were washed with 10 mL of 1N HCl, 10 mL of water and 10 ml of brine, dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by flash chromatography (SiO2, 10% ethyl acetate in hexanes) to yield 0.035 g of 7-[3-(4-methoxycarbonyl-phenyl)-1-pentyl-prop-2-ynyl]-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester.

Workup

  1. customwas degassed
  2. extractionextracted with three 10 mL portions of ethyl acetate
  3. washThe combined organic extracts were washed with 10 mL of 1N HCl, 10 mL of water and 10 ml of brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil
  8. customThe product was purified by flash chromatography (SiO2, 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9fbc8f8b983b4f9ab46bdfac091a6df0
Source dataset
uspto-grants-2004_11
Patent number
US06818652B2

Reaction notes

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