Methanol → 4-(4-Phenylamino-[1,3,5]triazin-2-yl)-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester

HRID 2217182ノート

反応式

HRID 2217182 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]([S:19]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=2[CH3:30])(=[O:21])=[O:20])[CH:7]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:9]=1)=[O:4].Cl[C:32]1[N:37]=[CH:36][N:35]=[C:34]([NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:33]=1.C(=O)([O-])[O-].[Na+].[Na+].CO>C(OCC)(=O)C.C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[N:6]([S:19]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=2[CH3:30])(=[O:20])=[O:21])[CH:7]=[C:8]([C:36]2[N:35]=[C:34]([NH:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:33]=[CH:32][N:37]=2)[CH:9]=1)=[O:4]

参加物

7

反応物 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 199377234-chloro-N-phenyl-1,3,5-triazin-2-amineHCID 59767810Methyl 1-(mesitylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate

生成物 1

HCID 597678114-(4-Phenylamino-[1,3,5]triazin-2-yl)-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester収率 33.9%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

In a 10 mL flask was added 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester (1.0 equivalent, 0.34 mmol, 149 mg), (4-chloro-[1,3,5]triazin-2-yl)-phenyl-amine (1.1 equivalent, 0.37 mmol, 78 mg), tetrakistriphenylphosphine palladium (0.2 equivalent, 0.07 mmol, 80 mg), sodium carbonate (1 mL, 2 N), methanol (1 mL) and benzene (5 mL). The resulting mixture was heated at 80° C. for 2 hours then diluted in ethyl acetate and washed with water, brine. The organic layer was dried over sodium sulfate then concentrated under vacuum. The crude mixture was then purified by prep HPLC to afford 55 mg of the title compound. HPLC, Rt=8.8 min, FIA, ES+=478.1.

後処理

  1. washwashed with water, brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationthen concentrated under vacuum
  4. customThe crude mixture was then purified by prep HPLC

出典と根拠

ORDレコード
ord-693e2d5d9747448bbd0429d061475fe0
出典データセット
uspto-grants-2008_08
特許番号
US07407962B2

反応ノート

読み込み中…