Ethyl 4-iodobenzoate → HCID 19963736, compound

HRID 52449Notes

Reaction equation

HRID 52449 reaction equation
[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[CH:13])=[CH:9][CH:10]=2)[NH:5][CH:4]([O:14][CH:15]([CH3:17])[CH3:16])[CH2:3]1.I[C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=1>C(NCC)C.[Cu]I.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>[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][C:20]3[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=3)=[CH:9][CH:10]=2)[N:5]=[C:4]([O:14][CH:15]([CH3:16])[CH3:17])[CH2:3]1

Participants

6

Reactant 2

HCID 142891Ethyl 4-iodobenzoateHCID 199637064,4-Dimethyl-2-isopropoxy-1,2,3,4-tetrahydro-7-ethynylquinoline2×

Product 1

HCID 19963736HCID 19963736, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

To a solution of 0.097 g (0.40 mmol) of 4,4-dimethyl-2-isopropoxy-1,2,3,4-tetrahydro-7-ethynylquinoline (Compound 27) and 1.16 g (0.75 ml, 4.2 mmol) of ethyl 4-iodobenzoate in 3.0 ml of diethylamine which was degassed under argon for 15 min, was added 0.043 g (0.23 mmol) of copper(I) iodide and then 0.064 g (0.09 mmol) of bis(triphenylphosphine)palladium(II) chloride. The reaction was stirred at room temperature for 16 h. The reaction mixture was then concentrated. Purification by flash chromatography (1.5% EtOAc in hexane) gave the title compound as an oil. PNMR (CDCl3) d 8.00 (2H, d, J=8.2 Hz), 7.54 (2H, d, J=8.1 Hz), 7.32 (1H, s), 7.23 (2H, s), 5.40 (1H, p, J=6.3 Hz), 4.37 (2H, q, J=7.1 Hz), 2.24 (2H, s), 1.39 (3H, t, J=7.1 Hz), 1.32 (6H, d, J=6.2 Hz), 1.24 (6H, s).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customPurification by flash chromatography (1.5% EtOAc in hexane)

Sources & evidence

ORD record
ord-da262a4a015e4cd1ac42e7bfcd61d789
Source dataset
uspto-grants-1997_04
Patent number
US05616712

Reaction notes

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