Toluene → HCID 89589799, compound

HRID 2200860Notes

Reaction equation

HRID 2200860 reaction equation
C1(C)C=CC=CC=1.Cl[C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[CH2:19][N:20]([CH3:37])[C:21](=[O:36])[N:22]([CH:23]4[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]4)[C:12]=3[C:11]=2[N:10]=1.[CH3:38][O:39][C:40]1[N:45]=[CH:44][C:43](B(O)O)=[CH:42][CH:41]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:38][O:39][C:40]1[N:45]=[CH:44][C:43]([C:9]2[CH:18]=[CH:17][C:16]3[N:15]=[CH:14][C:13]4[CH2:19][N:20]([CH3:37])[C:21](=[O:36])[N:22]([CH:23]5[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]5)[C:12]=4[C:11]=3[N:10]=2)=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 89589801HCID 89589801, compound

Product 1

HCID 89589799HCID 89589799, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the mixture of toluene (6 mL) and ethanol (2 mL) were dissolved tert-butyl 4-(9-chloro-3-methyl-2-oxo-3,4-dihydropyrimido[5,4-c][1,5]naphthyridin-1 (2H)-yl)piperidine-1-carboxylate (0.104 g, 0.241 mmol) and 6-methoxypyridine-3-boronic acid (40.7 mg, 0.266 mmol). To the solution were added tetrakis triphenylphosphine palladium (0) (5 mg) and aqueous sodium carbonate (2 N, 0.36 mL). The mixture was reacted under reflux under the protection of nitrogen for 16 h, then cooled to ambient temperature and filtrated. The organic phase was concentrated under reduced pressure, dissolved in DCM, washed sequentially with water and brine, dried over sodium sulfate, concentrated and purified by silica gel column chromatography (ethyl acetate/petroleum ether=2/1) to give the product (75 mg, 61.7% yield).

Workup

  1. customThe mixture was reacted
  2. temperatureunder reflux under the protection of nitrogen for 16 h
  3. filtrationfiltrated
  4. concentrationThe organic phase was concentrated under reduced pressure
  5. dissolutiondissolved in DCM
  6. washwashed sequentially with water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography (ethyl acetate/petroleum ether=2/1)

Sources & evidence

ORD record
ord-8769cc926160479d9c2214b9013c2176
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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