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

HRID 472961
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HRID 472961 반응식
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
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참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 178418476
HCID 178418476, 화합물
촉매
HCID 962Water용매
HCID 6344Dichloromethane용매
HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

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)+.

후처리

  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%)

출처 및 근거

ORD 기록
ord-f1b6e92e311240f98b7d0aa0b51427b1
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08633212B2

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