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

HRID 912585

반응식

HRID 912585 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 11180781trans-Bis(dicyclohexylamine)palladium(II) acetate촉매

반응 조건

온도
100 °C

실험 절차

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]+

후처리

  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%

출처 및 근거

ORD 기록
ord-e18caa7accb84a58a529e970ea4ce174
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026237B2

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