Sodium Carbonate → 1-[3-Bromo-4-methyl-5-(3-pyridyl)phenylcarbamoyl]-5-methoxy-6-trifluoromethylindoline

HRID 1977768Notes

Reaction equation

HRID 1977768 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([O:26][CH3:27])=[C:19]([C:22]([F:25])([F:24])[F:23])[CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH:5]=[C:6](Br)[C:7]=1[CH3:8].[N:28]1[CH:33]=[CH:32][CH:31]=[C:30](B(O)O)[CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([O:26][CH3:27])=[C:19]([C:22]([F:24])([F:25])[F:23])[CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH:5]=[C:6]([C:30]2[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=2)[C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 180050891-(3,5-Dibromo-4-methylphenylcarbamoyl)-5-methoxy-6-trifluoromethylindoline

Product 1

HCID 180051001-[3-Bromo-4-methyl-5-(3-pyridyl)phenylcarbamoyl]-5-methoxy-6-trifluoromethylindolineYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 1-(3,5-dibromo-4-methylphenylcarbamoyl)-5-methoxy-6-trifluoromethylindoline (D25, 0.51 g, 1 mmol), 3-pyridylboronic acid (0.12 g, 1 mmol), tetrakis (triphenylphosphine)palladium (0) (35 mg, 0.03 mmol) and sodium carbonate (0.41 g, 4 mmol) in dimethoxyethane (30 mL) and water (3 mL) was heated under reflux, under argon, for 18 h. The mixture was cooled and poured into water. The precipitate was filtered off, washed with water and dried. The crude product was chromatographed on silica gel, eluted with ethyl acetate, and the eluted material was triturated with ether to give the title compound (0.14 g, 28%), m.p. 216-8° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux, under argon, for 18 h
  3. temperatureThe mixture was cooled
  4. filtrationThe precipitate was filtered off
  5. washwashed with water
  6. customdried
  7. customThe crude product was chromatographed on silica gel
  8. washeluted with ethyl acetate
  9. customthe eluted material was triturated with ether

Sources & evidence

ORD record
ord-67b53d9bb3ca466f825184c91b2e26b4
Source dataset
uspto-grants-2001_05
Patent number
US06235758B1

Reaction notes

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