3-Nitrophenylboronic Acid → 8-(3-Nitrophenyl)-1,7-naphthyridin-6-amine

HRID 369025Notes

Reaction equation

HRID 369025 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10](Br)[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.C([O-])([O-])=O.[Na+].[Na+].[N+:19]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)([O-:21])=[O:20]>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:19]([O-:21])=[O:20])[CH:27]=3)[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 107043358-Bromo-1,7-naphthyridin-6-amine

Product 1

HCID 106117788-(3-Nitrophenyl)-1,7-naphthyridin-6-amine

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 6-amino-8-bromo-1,7-naphthyridine (4 g, 0.018 mol) in a mixture of tetrahydrofuran (80 ml) and aqueous Na2CO3 (34 ml, 2N) is added bis(dibenzylideneacetone)palladium (0.40 g, 0.0007 mol), triphenylphosphene (0.37 g, 0.0014 mol) and 3-nitrophenylboronic acid (3.7 g, 0.022 mol). The mixture is stirred for 16 h at 80° C. The mixture is filtered, ethyl acetate added and the mixture washed with 2N NaOH and water. The organic solvent is removed and the residue suspended in ether. Filtration affords the title compound. Mass M+H 267. mp 221-223° C.

Workup

  1. filtrationThe mixture is filtered
  2. additionethyl acetate added
  3. washthe mixture washed with 2N NaOH and water
  4. customThe organic solvent is removed
  5. filtrationFiltration

Sources & evidence

ORD record
ord-0662147adec24a0ea526eee25062df1e
Source dataset
uspto-grants-2000_10
Patent number
US06136821

Reaction notes

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