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

HRID 1272477ノート

反応式

HRID 1272477 の反応式
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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 9832798Tris(dibenzylideneacetone) dipalladium触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-79a643f4c76e4642b8ade773969d58c0
出典データセット
uspto-grants-2007_04
特許番号
US07208493B2

反応ノート

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