Sodium Carbonate → HCID 22118889, compound

HRID 1275013Notes

Reaction equation

HRID 1275013 reaction equation
Cl.Br[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)[CH:17]=1)=[O:14].[N:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:13]([C:8]2[C:9]3[C:4](=[C:3]([C:34]4[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=4)[CH:12]=[CH:11][CH:10]=3)[CH:5]=[CH:6][CH:7]=2)=[O:14])=[CH:17][C:18]=1[N:24]1[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 22118923HCID 22118923, compound

Product 1

HCID 22118889HCID 22118889, compoundYield 17.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred suspension of 5-bromo-N-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]naphth-1-yl carboxamide hydrochloride salt (E2, 0.35 g, 0.71 mmole) and 4-pyridylboronic acid (85 mg, 0.71 mmole) in 1,2-dimethoxyethane (30 ml) and water (30 ml) containing sodium carbonate (0.38 g, 3.5 mmole) was de-gassed by bubbling argon through for 15 minutes. Tetrakis (triphenylphosphine)palladium (0) (80 mg) was added and the mixture heated at reflux for 30 h. The mixture was concentrated in vacuo to approx. 30 ml volume, then diluted with water (50 ml) and extracted with dichloromethane. The organic extract was dried (Na2SO4) and concentrated in vacuo to a dark solid. Purification by column chromatography on silica gel eluting with 0-20% methanol/dichloromethane afforded the title compound as a pale yellow oil (55 mg, 17%). This was converted to its hydrochloride salt and solidified from acetone.

Workup

  1. customwas de-gassed
  2. customby bubbling argon through for 15 minutes
  3. additionTetrakis (triphenylphosphine)palladium (0) (80 mg) was added
  4. temperaturethe mixture heated
  5. temperatureat reflux for 30 h
  6. concentrationThe mixture was concentrated in vacuo to approx. 30 ml volume
  7. additiondiluted with water (50 ml)
  8. extractionextracted with dichloromethane
  9. extractionThe organic extract
  10. dry with materialwas dried (Na2SO4)
  11. concentrationconcentrated in vacuo to a dark solid
  12. customPurification by column chromatography on silica gel eluting with 0-20% methanol/dichloromethane

Sources & evidence

ORD record
ord-b94ea30169cd4c21bea95a96941d1817
Source dataset
uspto-grants-2000_12
Patent number
US06159979

Reaction notes

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