Potassium Carbonate → 7-(2,6-dimethylphenyl)-5-methyl-N-phenylbenzo[e][1,2,4]triazin-3-amine

HRID 1272478Notes

Reaction equation

HRID 1272478 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]=[CH:25][CH:24]=[C:23]([CH3:27])[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>[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:22]=1[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

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 5833222,6-Dimethylphenylboronic acidHCID 18455767(7-Bromo-5-methyl-benzo[1,2,4]triazin-3-yl)-phenyl-amine

Product 1

HCID 103826277-(2,6-dimethylphenyl)-5-methyl-N-phenylbenzo[e][1,2,4]triazin-3-amineYield 46.4%

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 (60 mg, 0.19 mmol) dissolved in 3 ml N,N-Dimethylacetamide in a 20 ml vial, 2,6-dimethyl-phenylboronic acid (114 mg, 0.76 mmol) dissolved in 2 ml ethanol and potassium carbonate (31 mg, 0.3 mmol) dissolved in 1 ml water were added. Triphenylphosphine (4.5 mg, 0.0171 mmol) and tris(dibenzylideneacetone) dipalladium (0) (4.5 mg, 4.9 umol) were added to the mixture. The mixture was reflux overnight. The crude product was filtered and purified by preparative HPLC. 30 mg [7-(2,6-Dimethyl-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-phenyl-amine was isolated. Yield: 46%; ESI-MS: [M+H]+, 341; 1H NMR (DMSO-d6): δ 2.05 (s, 6 H), 2.67(s, 3H), 7.07(t, J=7.33 Hz, 1 H), 7.17–7.24 (m, 3 H), 7.41 (t, J=7.56 Hz, 2 H), 7.62 (d, J=1.49 Hz, 1 H), 7.93 (d, J=1.49 Hz, 1 H), 8.05 (d, J=7.72 Hz, 1H).

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-b57a364782214d8f9911ab9a7953fd63
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

Loading…