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

HRID 273505

반응식

HRID 273505 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 86587095Dimethoxyethane ethanol water용매

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온도
100 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-2554428ba5d54cd4a7d3ae2361dc0a0c
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456176B2

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