Tetrahydrofuran → HCID 178451290, compound

HRID 1868930Notes

Reaction equation

HRID 1868930 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:26])[C:7]([C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])=[C:8]([OH:14])[C:9]2([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C1COCC1.C(N(C(C)C)C(C)C)C.[C:41]1([C:47]#[CH:48])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CCOC(C)=O.[Cu]I>[OH:14][C:8]1[C:9]([CH3:12])([CH3:13])[C:10]2[C:5]([C:6](=[O:26])[C:7]=1[C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])=[O:16])=[CH:4][CH:3]=[C:2]([C:48]#[C:47][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH:11]=2

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10821PhenylacetyleneHCID 81531DiisopropylethylamineHCID 178451288HCID 178451288, compound

Product 1

HCID 178451290HCID 178451290, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of tert-butyl 2-(7-bromo-2-hydroxy-1,1-dimethyl-4-oxo-1,4-dihydronaphthalene-3-carboxamido)acetate (120 mg, 283 μmol, Example 53A-E), palladium dichloride bistriphenylphosphine (20 mg, 28 μmol), and copper(I) iodide (11 mg, 57 μmol) was added THF (1414 μL), N-ethyl-N-isopropylpropan-2-amine (148 μL, 848 μmol), and phenylacetylene (62 μL, 566 μmol). The reaction was heated at 80° C. for 2 hours. The reaction mixture was diluted with 100 mL of EtOAc, washed 2 times with 75 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated to give crude product which was purified via flash chromatography to give the title compound.

Workup

  1. washwashed 2 times with 75 mL of sodium bicarbonate (saturated, aqueous)
  2. customseparated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give crude product which
  6. customwas purified via flash chromatography

Sources & evidence

ORD record
ord-6df12b79390649439fc4db11ee2f850b
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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