Indole → HCID 13339549, compound

HRID 1723552Notes

Reaction equation

HRID 1723552 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[F:10][C:11]1[CH:16]=[C:15](Br)[CH:14]=[CH:13][C:12]=1[O:18][CH3:19].C([O-])([O-])=O.[K+].[K+].O>CN1CCCC1=O>[F:10][C:11]1[CH:16]=[C:15]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH:14]=[CH:13][C:12]=1[O:18][CH3:19]

Participants

6

Reactant 4

HCID 798IndoleHCID 962WaterHCID 11430Potassium CarbonateHCID 753784-Bromo-2-fluoroanisole

Product 1

HCID 13339549HCID 13339549, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Indole (60 g, 0.51 mole), o-fluoro-p-bromoanisole (112.2 g, 0.547 mole), K2CO3 (76 g, 0.55 mole) and Cu2Br2 (14 g) were combined in 600 ml N-methylpyrrolidone and heated at 185°-200° for 48 hours, stirring under N2. The reaction mixture was cooled, poured into ice and water and extracted several times with ethyl acetate. The combined organic layers were washed with H2O, then brine, dried over MgSO4, treated with activated carbon, and concentrated to an oil (148 g). A portion of the oil (25 g) was chromatographed on silica gel (7.5×18 cm) eluting with 1:9 CH2Cl2 :hexane, yielding title product as an oil which crystallized on standing in vacuo overnight, 7.2 g, m.p. 65°-67°.

Workup

  1. temperatureheated at 185°-200° for 48 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted several times with ethyl acetate
  4. washThe combined organic layers were washed with H2O
  5. dry with materialbrine, dried over MgSO4
  6. additiontreated with activated carbon
  7. concentrationconcentrated to an oil (148 g)
  8. customA portion of the oil (25 g) was chromatographed on silica gel (7.5×18 cm)
  9. washeluting with 1:9 CH2Cl2

Sources & evidence

ORD record
ord-3bc691466218477ab1b9a43b18c838f9
Source dataset
uspto-grants-1989_08
Patent number
US04861880

Reaction notes

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