Potassium Carbonate → 7-mesityl-5-methyl-N-phenylbenzo[e][1,2,4]triazin-3-amine

HRID 1272475Notes

Reaction equation

HRID 1272475 reaction equation
Br[C:2]1[CH:18]=[C:17]([CH3:19])[C:5]2[N:6]=[C:7]([NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:8]=[N:9][C:4]=2[CH:3]=1.[CH3:20][C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[C:22]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C(=O)C.C(O)C.O.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[CH3:19][C:17]1[C:5]2[N:6]=[C:7]([NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:8]=[N:9][C:4]=2[CH:3]=[C:2]([C:22]2[C:23]([CH3:28])=[CH:24][C:25]([CH3:27])=[CH:26][C:21]=2[CH3:20])[CH:18]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 2921842,4,6-Trimethylbenzeneboronic acidHCID 18455767(7-Bromo-5-methyl-benzo[1,2,4]triazin-3-yl)-phenyl-amine

Product 1

HCID 184557227-mesityl-5-methyl-N-phenylbenzo[e][1,2,4]triazin-3-amineYield 26.8%

Reagents, catalysts & solvents 4

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of (7-Bromo-5-methyl-benzo[1,2,4]triazin-3-yl)-phenyl-amine (10 mg, 0.032 mmol) dissolved in 2 ml N,N-Dimethylacetamide in a 20 ml vial, 2,4,6-trimethylphenylboronic acid (21 mg, 0.128 mmol) dissolved in 1 ml ethanol and potassium carbonate (6.4 mg, 0.06 mmol) dissolved in 1 ml water were added. Triphenylphosphine (1 mg, 0.0038 mmol) and tris(dibenzylideneacetone) dipalladium (0) (1 mg, 1.09 umol) were added to the mixture. The mixture was reflux overnight. The crude product was filtered and purified by preparative HPLC. 3 mg [5-Methyl-7-(2,4,6-trimethyl-phenyl)-benzo[1,2,4]triazin-3-yl]-phenyl-amine was isolated. Yield: 26.8%; ESI-MS: [M+H]+, 355; 1H NMR (CDCl3): δ 2.06 (s, 6 H), 2.36 (s, 3 H), 2.72 (s, 3 H), 6.99 (s, 2 H), 7.17 (m, 1 H), 7.45 (m, 2 H), 7.57 (m, 1 H), 7.89 (d, J=1.36 Hz, 1 H), 7.94(d, J=8.76 Hz, 2 H).

Workup

  1. additionwere added
  2. temperatureThe mixture was reflux overnight
  3. filtrationThe crude product was filtered
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-6f39b99e1dfb4368ac635821afe02e41
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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