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Nitrogen → 3-(3-Oxo-2,2',3,3',5',6'-hexahydrospiro[indene-1,4'-pyran]-5-yl)benzonitrile

HRID 1503377
ノート
印刷プレビュー

反応式

HRID 1503377 の反応式
C([O-])([O-])=O.[Cs+].[Cs+].Br[C:8]1[CH:9]=[C:10]2[C:19](=[CH:20][CH:21]=1)[C:13]1([CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)[CH2:12][C:11]2=[O:22].[C:23]([C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1)#[N:24].N#N>C(Cl)Cl.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.O.O1CCOCC1>[O:22]=[C:11]1[C:10]2[C:19](=[CH:20][CH:21]=[C:8]([C:29]3[CH:30]=[C:25]([CH:26]=[CH:27][CH:28]=3)[C:23]#[N:24])[CH:9]=2)[C:13]2([CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH2:12]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

9

反応物 4

HCID 947NitrogenHCID 10796Cesium carbonateHCID 27343253-Cyanophenylboronic acidHCID 581976775-bromo-2',3',5',6'-tetrahydrospiro[indene-1,4'-pyran]-3(2H)-one

生成物 1

HCID 665847103-(3-Oxo-2,2',3,3',5',6'-hexahydrospiro[indene-1,4'-pyran]-5-yl)benzonitrile収率 76.9%

試薬・触媒・溶媒 4

HCID 178418476
HCID 178418476、化合物
触媒
HCID 962Water溶媒
HCID 6344Dichloromethane溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a 10 mL CEM microwave test tube was charged with Cs2CO3 (147 mg, 0.45 mmol), PdCl2(PPh3)2 (20 mg, 0.028 mmol), 5-bromo-2′,3′,5′,6′-tetrahydrospiro[indene-1,4′-pyran]-3(2H)-one (51 mg, 0.18 mmol), 3-cyanophenylboronic acid (35 mg, 0.24 mmol), dioxane (3 mL) and H2O (0.1 mL), the system was swept with N2 and capped, and heated in a CEM microwave reactor at 100° C. for 10 min. The reaction mixture was diluted with DCM, washed with brine, dried over anhydrous Na2SO4, and filtered, and concentrated. The residue was purified by flash chromatography on silica gel eluting with EA in hexane (0-30%) to give 42 mg of 3-(3-oxo-2,2′,3,3′,5′,6′-hexahydrospiro[indene-1,4′-pyran]-5-yl)benzonitrile as white solid. MS ESI+ve m/z 304 (M+H)30.

後処理

  1. customcapped
  2. washwashed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel eluting with EA in hexane (0-30%)

出典と根拠

ORDレコード
ord-f0e0bb1bf9b44fee932451987d18cfc9
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09212153B2

反応ノート

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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