Potassium Hydroxide → 1,4-dimethyl-5-(2-phenoxy-phenyl)-1H-pyrrole-3-carboxylic acid (4-methanesulfonyl-phenyl)-amide

HRID 912585

反応式

HRID 912585 の反応式
[S:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[C:15]([CH3:21])=[C:16](Br)[N:17]([CH3:19])[CH:18]=2)=[O:13])=[CH:7][CH:6]=1)(=[O:4])(=[O:3])N.[O:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[K+].[CH2:40](O)C.CN(C=O)C>CC(O)=O.CC(O)=O.C1CCC([N-]C2CCCCC2)CC1.C1CCC([N-]C2CCCCC2)CC1.[Pd+2]>[CH3:40][S:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[C:15]([CH3:21])=[C:16]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:17]([CH3:19])[CH:18]=2)=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

参加物

6

反応物 4

HCID 14797Potassium HydroxideHCID 2773559(2-Phenoxyphenyl)boronic acidHCID 19794673N,N-dimethylformamide ethanolHCID 672538152-Bromo-1,3-dimethyl-1H-pyrrole-4-carboxylic acid [4-(sulfamoyl)phenyl]-amide

生成物 1

HCID 598076411,4-dimethyl-5-(2-phenoxy-phenyl)-1H-pyrrole-3-carboxylic acid (4-methanesulfonyl-phenyl)-amide収率 8%

試薬・触媒・溶媒 1

HCID 11180781trans-Bis(dicyclohexylamine)palladium(II) acetate触媒

反応条件

温度
100 °C

実験手順

Into a 50 mL round bottom flask was weighed 100 mg of 2-Bromo-1,3-dimethyl-1H-pyrrole-4-carboxylic acid [4-(sulfamoyl)phenyl]-amide (0.27 mmol), 230 mg of (2-phenoxy)phenylboronic acid, potassium hydroxide (30.2 mg, 0.54 mmol), and DAPCy (J. Org Chem (2004), 69: 4330-4335) (6.2 mg, 4 Mol %) and Ethanol/DMF (3 ml, 50:50) was added. The solution was heated at 100° C. overnight. The reaction was cooled and washed into a separatory funnel with ethyl acetate and water. The ethyl acetate washed with water and brine, then was dried (MgSO4), and concentrated in vacuo. The resulting residue was purified by flash chromatography (SiO2), eluting with EtOAc/Hex 0-80% to afford the title compounds as a white solid (10 mg, 8%); 1H NMR (DMSO-d6): δ 7.88 (d, J=9 Hz, 2H), 7.77 (d, J=9 Hz, 2H), 7.60 (s, 1H), 7.43-7.37 (m, 1H), 7.32-7.20 (m, 4H), 7.04 (d, J=9 Hz, 2H), 6.85 (d, J=8 Hz, 2H), 3.52 (s, 3H), 3.04 (s, 3H), 2.20 (s, 3H); MS (ESI) m/z 461 [M+H]+

後処理

  1. customInto a 50 mL round bottom flask was weighed
  2. temperatureThe reaction was cooled
  3. washwashed into a separatory funnel with ethyl acetate and water
  4. washThe ethyl acetate washed with water and brine
  5. dry with materialwas dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by flash chromatography (SiO2)
  8. washeluting with EtOAc/Hex 0-80%

出典と根拠

ORDレコード
ord-e18caa7accb84a58a529e970ea4ce174
出典データセット
uspto-grants-2011_09
特許番号
US08026237B2

関連ノート

読み込み中…