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

HRID 273526Notes

Reaction equation

HRID 273526 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.[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-842881aa5d7e41b7bef1528e8793fca7
Source dataset
uspto-grants-2008_11
Patent number
US07456176B2

Reaction notes

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