Benzophenone imine → HCID 59352111, compound

HRID 2385558Notes

Reaction equation

HRID 2385558 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3([C:29]4[C:20](=[CH:21][C:22]5[O:27][CH2:26][CH2:25][O:24][C:23]=5[CH:28]=4)[O:19][CH2:18]3)[C:10]2=[O:30])[CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].[C:37](=[NH:50])([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>COCCOC.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:38]1([C:37](=[N:50][C:2]2[N:7]=[C:6]([CH2:8][N:9]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]4([C:29]5[C:20](=[CH:21][C:22]6[O:27][CH2:26][CH2:25][O:24][C:23]=6[CH:28]=5)[O:19][CH2:18]4)[C:10]3=[O:30])[CH:5]=[CH:4][CH:3]=2)[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 3

HCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 59352412HCID 59352412, compound

Product 1

HCID 59352111HCID 59352111, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1′-[(6-chloropyridin-2-yl)methyl]-2,3-dihydrospiro[furo[2,3-g][1,4]-benzodioxine-8,3′-indol]-2′(1′H)-one (0.2 g, 0.5 mmol) and sodium tert-butoxide (0.06 g, 0.67 mmol) in 1,2-dimethoxyethane (3 mL) was degassed with argon for 15 min. (R)-(−)-1′-[(S)-2-(dicyclohexylphosphino)ferrocenyl}ethyldi-tert-butylphosphine (0.006 g, 0.01 mmol), palladium(II) acetate (0.01 g, 0.05 mmol), and benzophenone imine (0.1 mL, 0.6 mmol) were added. The reaction mixture was stirred at 70° C. for 24 h, allowed to cool to ambient temperature, diluted with dichloromethane (20 mL) and filtered through a pad of diatomaceous earth. The pad was washed with dichloromethane (20 mL) and the filtrate was concentrated in vacuo. The residue was purified by column chromatography and eluted with a 25% to 35% gradient of ethyl acetate in hexanes to afford 1′-({6-[(diphenylmethylidene)amino]pyridin-2-yl}methyl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.19 g, 70%) as a colorless solid: MS (ES+) m/z 565.8 (M+1).

Workup

  1. additionwere added
  2. temperatureto cool to ambient temperature
  3. filtrationfiltered through a pad of diatomaceous earth
  4. washThe pad was washed with dichloromethane (20 mL)
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. washeluted with a 25% to 35% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2196d298c434413d93afbfe4bf301309
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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