Dichloromethane → 7-(2-Chloro-5-methoxyphenyl)-5-methylbenzo[e][1,2,4]triazin-3-amine

HRID 273505

反応式

HRID 273505 の反応式
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.[C:14]([O-:17])([O-])=O.[Na+].[Na+].[CH2:20]([Cl:22])Cl>COCCOC.CCO.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[Cl:22][C:20]1[CH:11]=[CH:12][C:2]([O:17][CH3:14])=[CH:3][C:4]=1[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

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 248227527-Bromo-5-methylbenzo[e][1,2,4]triazin-3-amine

生成物 1

HCID 248227537-(2-Chloro-5-methoxyphenyl)-5-methylbenzo[e][1,2,4]triazin-3-amine

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 86587095Dimethoxyethane ethanol water溶媒

反応条件

温度
100 °C

実験手順

7-bromo-5-methyl-benzo[1,2,4]triazin-3-ylamine (33.47 mmol, 1.0 equiv), 1-chloro-4-methoxy-2-boronic acid (50.21 mmol, 1.5 equiv), Pd(PPH3)4 (3.347 mmol, 0.1 equiv), and Na2CO3 (133.9 mmol, 4.0 equiv) were dissolved in DME/EtOH/water 6:1:1 and refluxed at 100° C. under an argon blanket for 4 h. The reaction was cooled to room temperature, diluted with 100 mL DCM and filtered. The precipitate that was recovered was suspended in water, filtered and rinsed with ether. The precipitate afforded 7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine, as a green solid (8.37 g, 84% yield). Rf=0.85 (9:1 DCM/MeOH). 1H NMR (DMSO-d6): δ 3.35 (s, 6H), 7.01 (dd, J=8.8 Hz, J=3.0, 1H), 7.09 (d, J=3.0 Hz, 1H), 7.48 (d, J=8.8 Hz, 1H), 7.75 (bm, 2H). MS (ES+) m/z=303. LC retention time 3.03 min.

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered
  3. customThe precipitate that was recovered
  4. filtrationfiltered
  5. washrinsed with ether

出典と根拠

ORDレコード
ord-2554428ba5d54cd4a7d3ae2361dc0a0c
出典データセット
uspto-grants-2008_11
特許番号
US07456176B2

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