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

HRID 449222Notes

Reaction equation

HRID 449222 reaction equation
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+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-85f2bf12af704fb9b023f8d9362606a3
Source dataset
uspto-grants-2013_07
Patent number
US08481536B2

Reaction notes

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