Water → 1-(diphenylmethyl)-4-fluoro-1H-indole-2,3-dione

HRID 2385089Notes

Reaction equation

HRID 2385089 reaction equation
[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:8]2[C:16]3[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=3)[C:10](I)=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I([O-])(=O)(=O)=[O:26].[Na+].[OH2:31]>C(#N)C.C(OCC)(=O)C.O.[Ru](Cl)(Cl)Cl>[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:8]2[C:16]3[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=3)[C:10](=[O:31])[C:9]2=[O:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 673571561-(Diphenylmethyl)-3-iodo-4-fluoroindole

Product 1

HCID 685968111-(diphenylmethyl)-4-fluoro-1H-indole-2,3-dioneYield 25%

Reagents, catalysts & solvents 3

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(diphenylmethyl)-3-iodo-4-fluoroindole (8.85 g, 20.7 mmol) in a mixture of acetonitrile (25 mL) and water (5 mL) was added ruthenium (III) chloride monohydrate (0.30 g, 1.45 mmol) and sodium periodate (13.3 g, 62.2 mmol). The reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was diluted with ethyl acetate (100 mL), washed with water (3×25 mL), saturated aqueous ammonium chloride (3×25 mL) and brine (3×25 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was crystallized from acetonitrile to afford 1-(diphenylmethyl)-4-fluoro-1H-indole-2,3-dione (1.73 g, 25%) as an orange solid: mp 168-171° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.49-7.41 (m, 1H), 7.38-7.28 (m, 10H), 6.86 (dd, J=8.8, 8.8 Hz, 1H), 6.80 (s, 1H), 6.45 (d, J=8.1 Hz, 1H); 13C NMR (75 MHz, DMSO-d6) δ 178.3, 157.8, 157.7 (d, 1JC-F=261.0 Hz), 150.6 (d, 3JC-F=6.0 Hz), 139.7 (d, 2JC-F=10.0 Hz), 137.0, 128.5, 128.3, 127.8, 110.7 (d, 2JC-F=19.5 Hz), 108.8 (d, 4JC-F=2.9 Hz), 106.4 (d, 3JC-F=18.2 Hz), 28.7; MS (ES+) m/z 332.2 (M+23).

Workup

  1. washwashed with water (3×25 mL), saturated aqueous ammonium chloride (3×25 mL) and brine (3×25 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-0fc35d7957e94cdda6826c73440f3acc
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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