3-Nitrophenylboronic Acid → 5-Methyl-7-(3-nitro-phenyl)-benzo[1,2,4]triazin-3-ylamine

HRID 273526

反応式

HRID 273526 の反応式
Br[C:2]1[CH:12]=[C:11]([CH3:13])[C:5]2[N:6]=[C:7]([NH2:10])[N:8]=[N:9][C:4]=2[CH:3]=1.[N+:14]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)([O-:16])=[O:15].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][C:11]1[C:5]2[N:6]=[C:7]([NH2:10])[N:8]=[N:9][C:4]=2[CH:3]=[C:2]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:14]([O-:16])=[O:15])[CH:22]=2)[CH:12]=1

参加物

5

反応物 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 248227527-Bromo-5-methylbenzo[e][1,2,4]triazin-3-amine

生成物 1

HCID 598376075-Methyl-7-(3-nitro-phenyl)-benzo[1,2,4]triazin-3-ylamine収率 73%

試薬・触媒・溶媒 1

HCID 178418397HCID 178418397、化合物触媒

実験手順

An oven dried 25 mL round bottom flask was charged with 7-bromo-5-methyl-benzo[1,2,4]triazin-3-ylamine (1.05 g, 4.49 mmol, 1 equiv), 3-Nitro phenyl boronic acid (1.05 g, 6.29 mmol, 1.4 equiv), sodium carbonate (1.9 g, 18 mmol, 4 equiv) and tetrakis(triphenylphosphine)palladium(0) (0.519 g, 0.449 mmol, 0.1 equiv). The reactants were flushed with argon and diluted with ethylene glycol dimethyl ether (6 mL), ethanol (1 mL) and DI water (1 mL). The reaction vessel was outfitted with condenser and refluxed for 2.5 hours. The reaction was cooled to ambient temperature and diluted with water. The resulting precipitate was filtered off, washed thoroughly with water and dried. Brown solids (0.9 g, 73% yield). MS (ESI+): m/z=282.4, LC retention time: 2.77 min.

後処理

  1. customAn oven dried 25 mL round bottom flask
  2. customThe reactants were flushed with argon
  3. additiondiluted with ethylene glycol dimethyl ether (6 mL), ethanol (1 mL) and DI water (1 mL)
  4. customThe reaction vessel was outfitted with condenser
  5. temperaturerefluxed for 2.5 hours
  6. additiondiluted with water
  7. filtrationThe resulting precipitate was filtered off
  8. washwashed thoroughly with water
  9. customdried

出典と根拠

ORDレコード
ord-842881aa5d7e41b7bef1528e8793fca7
出典データセット
uspto-grants-2008_11
特許番号
US07456176B2

関連ノート

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