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Diisopropylethylamine → 4-[3-(2-Oxo-1,2-dihydro-quinolin-6-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

HRID 2075687
ノート
印刷プレビュー

反応式

HRID 2075687 の反応式
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.[SH:13][C:14]1[CH:15]=[C:16]([C:20]2([C:26]#[N:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:17]=[CH:18][CH:19]=1.CCN(C(C)C)C(C)C.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:12]=[C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([S:13][C:14]3[CH:15]=[C:16]([C:20]4([C:26]#[N:27])[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)[CH:17]=[CH:18][CH:19]=3)[CH:3]=2)[NH:8]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 138361846-Iodoquinolin-2(1H)-oneHCID 187863864-(3-Mercapto-phenyl)-tetrahydro-pyran-4-carbonitrile

生成物 1

HCID 589265284-[3-(2-Oxo-1,2-dihydro-quinolin-6-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

6-Iodo-1H-quinolin-2-one (5.13 g, 18.9 mmol) and 4-(3-Mercapto-phenyl)-tetrahydro-pyran-4-carbonitrile (5f, 4.57 g, 20.8 mmol) were dissolved in 1,4-dioxane (160 mL) and degassed for 10 minutes with N2. iPr2NEt (6.6 mL, 37.9 mmol) was added, followed by Pd2dba3 (434 mg, 0.47 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (548 mg, 0.95 mmol), and the reaction was degassed for another 10 minutes with N2. The reaction was then sealed and heated to 80° C. overnight. After cooling to room temperature, the reaction was filtered and concentrated, and the residue was purified by silica gel chromatography (0-100% MeOH in EtOAc) to give the desired product, 5g.

後処理

  1. customdegassed for 10 minutes with N2
  2. customthe reaction was degassed for another 10 minutes with N2
  3. customThe reaction was then sealed
  4. temperatureAfter cooling to room temperature
  5. filtrationthe reaction was filtered
  6. concentrationconcentrated
  7. customthe residue was purified by silica gel chromatography (0-100% MeOH in EtOAc)

出典と根拠

ORDレコード
ord-5341f1e6db8c42228d0c75e225a9e457
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07919621B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート