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

HRID 472059

반응식

HRID 472059 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4d13ef449e57435595c7e644a27df280
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633193B2

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