Hydrochloric Acid → HCID 86673035, 화합물

HRID 1853266노트

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HRID 1853266 반응식
[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]

참가 물질

10

반응물 5

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

생성물 1

HCID 86673035HCID 86673035, 화합물수율 51.1%

시약·촉매·용매 4

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

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온도
90 °C

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-1afc103673ed42928e1518e50159ab79
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962627B2

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