Sodium Carbonate → 5-Nitro-3-phenyl-1H-indole

HRID 907128Notes

Reaction equation

HRID 907128 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[NH:4][CH:3]=1.[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:14]1([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=3)[NH:4][CH:3]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 431520843-Bromo-5-nitro-1H-indole

Product 1

HCID 6171745-Nitro-3-phenyl-1H-indoleYield 9%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 313Hydrochloric AcidSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 3-bromo-5-nitroindole from above (625 mg, 2.1 mmol), phenylboronic acid (381 mg, 3.13 mmol), triphenylphosphine (109.3 mg, 0.417 mmol) in dimethoxyethane (4.16 mL) was degassed. To this mixture 2N sodium carbonate (6.25 mL) was added, and reaction mixture was degassed again. To the reaction was added palladium (II) acetate (23.4 mg, 0.104 mmol), and the reaction was refluxed under dry nitrogen with stirring for 8 hours. The reaction mixture was then diluted with 1 M HCl (100 mL), and extracted with ethyl acetate (100 mL). The organic phase was washed with water (100 mL), and brine (100 mL). The organic phase was dried over MgSO4 and concentrated in vacuo. The crude product was purified by chromatography over silica gel (EtOAc/hexanes, 10/90) to afford 3-phenyl-5-nitroindole as an orange powder (45 mg, 9% yield).

Workup

  1. customreaction mixture
  2. customwas degassed again
  3. temperaturethe reaction was refluxed under dry nitrogen
  4. extractionextracted with ethyl acetate (100 mL)
  5. washThe organic phase was washed with water (100 mL), and brine (100 mL)
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography over silica gel (EtOAc/hexanes, 10/90)

Sources & evidence

ORD record
ord-80be7ed67a8b4c2f9ad91cfed9d5e834
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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