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

HRID 1009558Notes

Reaction equation

HRID 1009558 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) is degassed. To this mixture 2N sodium carbonate (6.25 mL) is added, and the reaction mixture is degassed again. To the reaction is added palladium (II) acetate (23.4 mg, 0.104 mmol), and the reaction is refluxed under dry nitrogen with stirring for 8 hours. The reaction mixture is then diluted with 1 M HCl (100 mL), and extracted with ethyl acetate (100 mL). The organic phase is washed with water (100 mL), and brine (100 mL). The organic phase is dried over MgSO4 and concentrated in vacuo. The crude product is 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. customthe reaction mixture is degassed again
  2. temperaturethe reaction is refluxed under dry nitrogen
  3. extractionextracted with ethyl acetate (100 mL)
  4. washThe organic phase is washed with water (100 mL), and brine (100 mL)
  5. dry with materialThe organic phase is dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by chromatography over silica gel (EtOAc/hexanes, 10/90)

Sources & evidence

ORD record
ord-aa2ed58a18664c9abac5b151bd1de947
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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