Sodium Carbonate → N-[3-(3-amino-5-methyl-benzo[1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide

HRID 273525

反応式

HRID 273525 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.[CH3:14][S:15]([NH:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)(=[O:17])=[O:16].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>[NH2:10][C:7]1[N:8]=[N:9][C:4]2[CH:3]=[C:2]([C:23]3[CH:24]=[C:19]([NH:18][S:15]([CH3:14])(=[O:16])=[O:17])[CH:20]=[CH:21][CH:22]=3)[CH:12]=[C:11]([CH3:13])[C:5]=2[N:6]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 27735353-Methylsulfonylaminophenylboronic acidHCID 248227527-Bromo-5-methylbenzo[e][1,2,4]triazin-3-amine

生成物 1

HCID 59837624N-[3-(3-amino-5-methyl-benzo[1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide収率 82%

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 (0.889 g, 3.72 mmol, 1 equiv), 3-(methylsulfonylamino) phenyl boronic acid (1.12 g, 5.21 mmol, 1.4 equiv), sodium carbonate (1.57 g, 14.9 mmol, 4 equiv) and tetrakis(triphenylphosphine)palladium(0) (0.43 g, 0.372 mmol, 0.1 equiv). The reactants were flushed with argon and diluted with ethylene glycol dimethyl ether (20 mL), ethanol (5 mL) and DI water (5 mL). The reaction vessel was outfitted with condenser and refluxed for 4 hours. The reaction was filtered hot and diluted with ethyl acetate. The Organic layer was isolated and concentrated to a dark residue. This was dissolved in DMF (6 mL) and slowly diluted with water so as to precipitate out the product. Solids were filtered off and dried to yield an orange solid (1 g, 82% yield).

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 (20 mL), ethanol (5 mL) and DI water (5 mL)
  4. customThe reaction vessel was outfitted with condenser
  5. temperaturerefluxed for 4 hours
  6. filtrationThe reaction was filtered hot
  7. additiondiluted with ethyl acetate
  8. customThe Organic layer was isolated
  9. concentrationconcentrated to a dark residue
  10. dissolutionThis was dissolved in DMF (6 mL)
  11. additionslowly diluted with water so as
  12. customto precipitate out the product
  13. filtrationSolids were filtered off
  14. customdried

出典と根拠

ORDレコード
ord-9a1edb7d233d4b0f909c2c1d1738825f
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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