Water → N*7*-(3,4,5-Trimethoxy-phenyl)-[1,5]naphthyridine-2,7-diamine

HRID 1256186Notes

Reaction equation

HRID 1256186 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([NH2:12])=[N:9]2)=[N:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23])[NH2:18].CC(C)([O-])C.[Na+].O>C1(C)C=CC=CC=1.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:25][O:24][C:20]1[CH:19]=[C:17]([NH:18][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][C:8]([NH2:12])=[N:9]3)=[N:4][CH:3]=2)[CH:16]=[C:15]([O:14][CH3:13])[C:21]=1[O:22][CH3:23]

Participants

8

Reactant 4

HCID 962WaterHCID 322853,4,5-TrimethoxyanilineHCID 23676156Sodium t-butoxideHCID 583105327-Bromo-1,5-naphthyridin-2-amine

Product 1

HCID 58310538N*7*-(3,4,5-Trimethoxy-phenyl)-[1,5]naphthyridine-2,7-diamineYield 17.2%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Under argon atmosphere, 200 mg (892 μmol, 1 eq) of 7-bromo-1,5-naphthyridin-2-ylamine, 196.3 mg (1.07 mmol, 1.2 eq) of 3,4,5-trimethoxyaniline, 2 mg (2.3 μmol, 0.0025 eq) tris(dibenzylideneacetone)dipalladium, 4 mg (6.7 μmol, 0.0075 eq) 2,2′-bis(diphenylphosphino)-1,1′-binaphtyl and 120 mg (1.24 mmol, 1.4 eq) of sodium terbutoxide were introduced in 6 mL of toluene. The mixture was stirred at 80° C. for 24 h. The mixture was allowed to reach it and water was added. Aqueous layer was extracted with methylene chloride. Organic layers were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by column chromatography using methylene chloride/ethanol: 96/4 as eluent. The solvent was evaporated to dryness to afford 50 mg of yellow powder with 17% yield.

Workup

  1. additionwas added
  2. extractionAqueous layer was extracted with methylene chloride
  3. dry with materialOrganic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography
  7. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-00184fe745624bf9899aea315d1694b2
Source dataset
uspto-grants-2013_06
Patent number
US08461178B2

Reaction notes

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