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

HRID 1256186ノート

反応式

HRID 1256186 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 634876Binap, (A+-)-触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-00184fe745624bf9899aea315d1694b2
出典データセット
uspto-grants-2013_06
特許番号
US08461178B2

反応ノート

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