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

HRID 425727
Notes
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Reaction equation

HRID 425727 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalyst
HCID 1140TolueneSolvent
HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-addd17e83a514b82a5938cda2bd23ce7
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08106087B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes