Potassium Carbonate → [7-(2-Fluoro-6-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-phenyl-amine

HRID 1272476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1272476
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.[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][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>[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[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

Komponenten

9

Edukt 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 3294524(2-Fluoro-6-methoxyphenyl)boronic acidHCID 18455767(7-Bromo-5-methyl-benzo[1,2,4]triazin-3-yl)-phenyl-amine

Produkt 1

HCID 18455758[7-(2-Fluoro-6-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-phenyl-amineAusbeute 17,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9832798Tris(dibenzylideneacetone) dipalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

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-Fluoro-6-methoxy-phenylboronic acid (22 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. 2 mg [7-(2-Fluoro-6-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-phenyl-amine was isolated. Yield: 17.5%; ESI-MS: [M+H]+, 361; 1H NMR (CDCl3): δ 2.73 (s, 3 H), 3.83 (s, 3 H), 6.83–6.86 (m, 2H), 7.14 (m, 1 H), 7.34 (m, 1 H), 7.45 (m, 2 H), 7.75(s, 1 H), 7.92(m, 2 H), 8.24(s, 1 H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ee7907328a164a9ea2b5e8dae5fbd579
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208493B2

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