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Benzophenone imine → 6-[(diphenylmethylene)amino-]-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 1259819
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HRID 1259819 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([CH2:23][O:24][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]3=[O:22].[C:25](=[NH:38])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.ClCCl.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[C:26]1([C:25](=[N:38][C:2]2[CH:7]=[CH:6][C:5]3[C:8]4([CH2:23][O:24][C:4]=3[CH:3]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]4=[O:22])[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 592634366-bromo-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)one

생성물 1

HCID 866090226-[(diphenylmethylene)amino-]-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

시약·촉매·용매 3

HCID 9832798
Tris(dibenzylideneacetone) dipalladium
촉매
HCID 1140Toluene용매
HCID 6344Dichloromethane용매

실험 절차

To a solution of 6-bromo-1′-pentylspiro[1-benzofuran-3,3′-indol]-2′(1′H)one (0.10 g, 0.26 mmol) in anhydrous toluene (5.00 mL) was added benzophenone imine (0.09 g, 0.52 mmol), sodium t-butoxide (0.03 g, 0.36 mmol), tris(dibenzylideneacetone) dipalladium(0) (0.01 g, 0.07 mmol) and (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (0.12 g, 0.19 mmol). The reaction mixture was refluxed for 16 h, cooled down to ambient temperature, diluted with dichloromethane (50.0 mL) and filtered through a celite bed. The filtrate was concentrated in vacuo to dryness to give the title compound which was used in next step without purification.

후처리

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. filtrationfiltered through a celite bed
  3. concentrationThe filtrate was concentrated in vacuo to dryness

출처 및 근거

ORD 기록
ord-04e08231e76f4b70a6e2a4025944ae35
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08466188B2

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