Hydrochloric Acid → HCID 86673035, compound

HRID 1853266Notes

Reaction equation

HRID 1853266 reaction equation
[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[O:10][C:9]([C:18]2[N:19]=[CH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(NCC)C.[CH3:52][Si:53]([C:56]#[CH:57])([CH3:55])[CH3:54].Cl>CN(C)C=O.C(#N)C.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)I>[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13]([C:57]#[C:56][Si:53]([CH3:55])([CH3:54])[CH3:52])=[CH:14][CH:15]=2)[O:10][C:9]([C:18]2[N:19]=[CH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 86673023HCID 86673023, compound

Product 1

HCID 86673035HCID 86673035, compoundYield 51.1%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 7-bromo-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (120 mg, 0.28 mmol), trans-dichlorobis(triphenylphosphine)palladium (19 mg, 0.028 mmol), copper iodide (10 mg, 0.056 mmol), triphenylphosphine (14 mg, 0.056 mmol) in a mixture of dimethylformamide (3 ml) and acetonitrile (3 ml) was degassed with argon for 10 min and then treated with diethylamine (42 μl, 0.40 mmol) and trimethylsilylacetylene (46 μl, 0.326 mmol). The solution was warmed to 90° C. for 20 hours and then poured onto a 0.5N aqueous solution of hydrogen chloride, extracted with ethyl acetate and purified by flash chromatography over silica gel (gradient cyclohexane/ethyl acetate: 20-50%) to yield 2-isoquinolin-3-yl-7-trimethylsilylethynyl-chromen-4-one O-tert-butyl oxime (63 mg, 50%) as a yellow solid. The solid was dissolved in methanol (10 ml) and treated with potassium carbonate (39 mg, 0.28 mmol) and stirred at room temperature for 18 hours. Methanol was evaporated and the residue was extracted with ethyl acetate washed with water and brine, dried over sodium sulfate and the solution concentrated to dryness to yield 7-ethynyl-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (49 mg, 89%) as beige solid.

Workup

  1. customwas degassed with argon for 10 min
  2. extractionextracted with ethyl acetate
  3. custompurified by flash chromatography over silica gel (gradient cyclohexane/ethyl acetate: 20-50%)

Sources & evidence

ORD record
ord-1afc103673ed42928e1518e50159ab79
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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