3-Cyanophenylboronic acid → 3-(1-oxo-1,3,3',4'-tetrahydro-1'H-spiro[indene-2,2'-naphthalene]-6-yl)benzonitrile

HRID 472955ノート

反応式

HRID 472955 の反応式
Br[C:2]1[CH:19]=[C:18]2[C:5]([CH2:6][C:7]3([C:17]2=[O:20])[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]3)=[CH:4][CH:3]=1.[C:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)#[N:22]>O1CCOCC1.C([O-])([O-])=O.[Cs+].[Cs+].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:20]=[C:17]1[C:7]2([CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8]2)[CH2:6][C:5]2[C:18]1=[CH:19][C:2]([C:27]1[CH:28]=[C:23]([CH:24]=[CH:25][CH:26]=1)[C:21]#[N:22])=[CH:3][CH:4]=2

参加物

6

反応物 2

HCID 27343253-Cyanophenylboronic acidHCID 581975836-Bromo-3',4'-dihydro-1'H-spiro[indene-2,2'-naphthalen]-1(3H)-one

生成物 1

HCID 665847763-(1-oxo-1,3,3',4'-tetrahydro-1'H-spiro[indene-2,2'-naphthalene]-6-yl)benzonitrile収率 20%

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

実験手順

6-Bromo-3′,4′-dihydro-1′H-spiro[indene-2,2′-naphthalen]-1(3H)-one (163 mg, 0.5 mmol), 3-cyanophenylboronic acid (147 g, 1 mmol) in [1,4]-dioxane (12 mL), Cs2CO3 (2 N, 3.2 mL), then Pd(PPh3)2Cl2 (5 mg, 0.01 mmol) was added under Ar2, the mixture was refluxed for 30 minutes. The reaction mixture was concentrated in vacuo to give the residue, which was purified by TLC to give 3-(1-oxo-1,3,3′,4′-tetrahydro-1′H-spiro[indene-2,2′-naphthalene]-6-yl)benzonitrile (35 mg, 6%).

後処理

  1. temperaturethe mixture was refluxed for 30 minutes
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give the residue, which
  4. customwas purified by TLC

出典と根拠

ORDレコード
ord-aded660add204825b923c83b2c42c1dd
出典データセット
uspto-grants-2014_01
特許番号
US08633212B2

反応ノート

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