Hydrochloric Acid → HCID 86673035、化合物

HRID 1853266ノート

反応式

HRID 1853266 の反応式
[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]

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 86673023HCID 86673023、化合物

生成物 1

HCID 86673035HCID 86673035、化合物収率 51.1%

試薬・触媒・溶媒 4

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-1afc103673ed42928e1518e50159ab79
出典データセット
uspto-grants-2015_02
特許番号
US08962627B2

反応ノート

読み込み中…