Sodium Cyanide → 1'-(Diphenylmethyl)-2'-oxo-1,2'-dihydrospiro[1-benzofuran-3,3'-indole]-6-carbonitrile

HRID 2385181Notes

Reaction equation

HRID 2385181 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([CH2:31][O:32][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[N:10]([CH:17]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:9]3=[O:30].[C-]#N.[Na+].[CH3:36][N:37]1CCCC1=O>C(OCC)(=O)C.O.O.O.O.O.O.[Ni](Cl)Cl>[C:18]1([CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]3([C:5]4[CH:6]=[CH:7][C:2]([C:36]#[N:37])=[CH:3][C:4]=4[O:32][CH2:31]3)[C:9]2=[O:30])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 13387N-methyl-2-pyrrolidoneHCID 461941846-bromo-1'-(diphenylmethyl)spiro[1-benzofuran-3,3'-indol]-2'(1H)-one

Product 1

HCID 593526441'-(Diphenylmethyl)-2'-oxo-1,2'-dihydrospiro[1-benzofuran-3,3'-indole]-6-carbonitrileYield 100%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 10 mL microwave reaction vessel was charged with 6-bromo-1′-(diphenylmethyl)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (0.51 g, 1.1 mmol), nickel chloride hexahydrate (0.25 g, 1.1 mmol), sodium cyanide (0.10 g, 2.1 mmol) and 1-methyl-2-pyrrolidinone (1 mL). The solution was irradiated at 200° C. for 20 min in a microwave reactor. The solution was allowed to cool to ambient temperature, diluted with ethyl acetate (25 mL) and filtered. The filtrate was washed with brine (3×15 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography and eluted with a 15% to 50% gradient of ethyl acetate in hexanes to afford 1′-(diphenylmethyl)-2′-oxo-1,2′-dihydrospiro[1-benzofuran-3,3′-indole]-6-carbonitrile (0.50 g, 100%) as a colorless solid: 1H NMR (300 MHz, CDCl3) 7.44-7.22 (m, 10H), 7.21-7.18 (m, 1H), 7.14-6.93 (m, 5H), 6.72 (d, J=7.8 Hz, 1H), 6.55 (d, J=7.5 Hz, 1H), 5.07 (d, J=9.2 Hz, 1H), 4.80 (d, J=9.2 Hz, 1H).

Workup

  1. customThe solution was irradiated at 200° C. for 20 min in a microwave reactor
  2. filtrationfiltered
  3. washThe filtrate was washed with brine (3×15 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluted with a 15% to 50% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-11094a82de4243aba23d99334fdfd473
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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