Sodium Carbonate → HCID 57426226, compound

HRID 1696409Notes

Reaction equation

HRID 1696409 reaction equation
Br[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:8]([N+:17]([O-:19])=[O:18])[CH:7]=[CH:6][CH:5]=2.[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>CCO.C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:8]([N+:17]([O-:19])=[O:18])[CH:7]=[CH:6][CH:5]=2

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 57426225HCID 57426225, compound

Product 1

HCID 57426226HCID 57426226, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

To a deoxygenated solution of ethyl (2-bromo-4-nitro-1H-indol-3-yl)acetate from Step B (250 mg, 0.76 mmol), 2-methylphenylboronic acid (156 mg, 1.15 mmol), and Na2CO3 (202 mg, 1.91 mmol) in EtOH (10 mL), toluene (10 mL) and H2O (0.5 mL) was added tetrakis(triphenylphosphine)palladium (44 mg, 0.038 mmol) and the resulting mixture was heated at reflux for 18 h. The cooled mixture was diluted with H2O (20 mL) and extracted with EtOAc (2×50 mL), and the combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CHCl3:EtOAc—100:0 to 80:20, to give the title compound. MS: m/z=339 (M+1).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 18 h
  3. extractionextracted with EtOAc (2×50 mL)
  4. dry with materialthe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of CHCl3

Sources & evidence

ORD record
ord-0d0af6b559264f74a182cf8e81d6d7d8
Source dataset
uspto-grants-2012_04
Patent number
US08163752B2

Reaction notes

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