Potassium Hydroxide → 4-[5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine-3-yl]-cyclohex-3-enecarboxylic acid

HRID 602561

反応式

HRID 602561 の反応式
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][NH:17][C:14]2=[CH:15][N:16]=1)[CH3:2].C[O:21][C:22]([CH:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)=[O:23].[OH-].[K+]>CO>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[C:19]([C:27]3[CH2:28][CH2:29][CH:24]([C:22]([OH:23])=[O:21])[CH2:25][CH:26]=3)=[CH:18][NH:17][C:14]2=[CH:15][N:16]=1)[CH3:2]

参加物

5

反応物 3

HCID 14797Potassium HydroxideHCID 226643Methyl 4-oxocyclohexanecarboxylateHCID 116732465-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine

生成物 1

HCID 671525894-[5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine-3-yl]-cyclohex-3-enecarboxylic acid収率 40.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A solution of 5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine (200 mg, 0.8 mmol) in MeOH (5 mL) is added to a stirring solution of 4-oxo-cyclohexanecarboxylic acid methyl ester (204 mg, 1.2 mmol) and KOH (163 mg, 2.9 mmol) in MeOH (10 mL) at room temperature. The mixture is heated at reflux for 24 hours. The solvent is removed to dryness in vacuo. The residue is mixed with water and adjusted pH to 7. The mixture is extracted with CH2Cl2 (2×10 mL). The organic layer is washed with brine, dried, and evaporated under reduce pressure to give 120 mg of crude product. The crude product is used for next step without further purification.

後処理

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 24 hours
  3. customThe solvent is removed to dryness in vacuo
  4. additionThe residue is mixed with water and adjusted pH to 7
  5. extractionThe mixture is extracted with CH2Cl2 (2×10 mL)
  6. washThe organic layer is washed with brine
  7. customdried
  8. customevaporated

出典と根拠

ORDレコード
ord-8b2fe47687784ce989b4de6b4be6b57d
出典データセット
uspto-grants-2011_03
特許番号
US07906528B2

関連ノート

読み込み中…