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

HRID 1503371노트

반응식

HRID 1503371 반응식
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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 10796Cesium carbonate용매HCID 312751,4-Dioxane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-884a65917fdb45ad8ea6953c72bb3d60
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212153B2

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