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

HRID 1272477노트

반응식

HRID 1272477 반응식
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][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[C:23]=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][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[C:23]=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

참가 물질

9

반응물 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 2734343(2,6-Dimethoxyphenyl)boronic acidHCID 18455767(7-Bromo-5-methyl-benzo[1,2,4]triazin-3-yl)-phenyl-amine

생성물 1

HCID 18455755[7-(2,6-Dimethoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-phenyl-amine수율 42.4%

시약·촉매·용매 4

HCID 9832798Tris(dibenzylideneacetone) dipalladium촉매HCID 702Ethanol용매HCID 962Water용매HCID 31374Dimethylacetamide용매

실험 절차

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, 2,6-dimethoxy-phenylboronic acid (23 mg, 0.126 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. 5 mg [7-(2,6-Dimethoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-phenyl-amine was isolated. Yield: 42.4%; ESI-MS: [M+H]+, 373; 1H NMR (CDCl3): δ 2.72 (s, 3 H), 3.78 (s, 6 H), 6.70 (d, J=8.4 Hz, 2 H), 7.13 (m, 1 H), 7.35 (t, J=8.38 Hz, 1 H), 7.44 (m, 2 H), 7.89 (m, 1 H), 7.92 (dd, J1=8.78 Hz, J2=2.02 Hz, 2 H), 8.18 (d, J=2.02 Hz, 1 H).

후처리

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

출처 및 근거

ORD 기록
ord-79a643f4c76e4642b8ade773969d58c0
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208493B2

반응 노트

불러오는 중…