3-Cyanophenylboronic acid → 3-(4-Methoxy-1'-oxo-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-6'-yl)benzonitrile

HRID 472974

反応式

HRID 472974 の反応式
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:16][CH2:15][CH:14]([O:17][CH3:18])[CH2:13][CH2:12]3)[C:8]2=[O:11])=[CH:4][CH:3]=1.[C:19]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)#[N:20]>C([O-])([O-])=O.[Cs+].[Cs+].O1CCOCC1.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>[CH3:18][O:17][CH:14]1[CH2:15][CH2:16][C:7]2([CH2:6][C:5]3[C:9](=[CH:10][C:2]([C:25]4[CH:26]=[C:21]([CH:22]=[CH:23][CH:24]=4)[C:19]#[N:20])=[CH:3][CH:4]=3)[C:8]2=[O:11])[CH2:12][CH2:13]1

参加物

6

反応物 2

HCID 27343253-Cyanophenylboronic acidHCID 581972636'-bromo-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-one

生成物 1

HCID 670441643-(4-Methoxy-1'-oxo-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-6'-yl)benzonitrile収率 46.4%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 10796Cesium carbonate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of 6′-bromo-4-methoxyspiro[cyclohexane-1,2′-inden]-1′(3′H)-one (40 mg, 0.130 mmol) and 3-cyanophenylboronic acid (30.5 mg, 0.208 mmol) in Cs2CO3 (2 M, 0.247 mL) and 1,4-dioxane (1.2 mL) under N2 was added Pd(PPh3)2Cl2 (7.5 mg). The mixture was stirred at 100° C. for 6 minutes. After cooled to room temperature, the organic layer was dried and concentrated to give the residue, which was purified by TLC to give 3-(4-methoxy-1′-oxo-1′,3′-dihydrospiro[cyclohexane-1,2′-indene]-6′-yl)benzonitrile (20 mg, 46%).

後処理

  1. temperatureAfter cooled to room temperature
  2. customthe organic layer was dried
  3. concentrationconcentrated
  4. customto give the residue, which
  5. customwas purified by TLC

出典と根拠

ORDレコード
ord-6e35da0fbb1048de942df736b721b9fb
出典データセット
uspto-grants-2014_01
特許番号
US08633212B2

関連ノート

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