Methyl 6-(5-benzyloxy-6-chloro-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate → Methyl 6-(6-chloro-5-hydroxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate

HRID 1191666노트

반응식

HRID 1191666 반응식
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[Cl:18])[N:14]([CH2:19][C:20]1[N:25]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[CH:23]=[CH:22][CH:21]=1)[C:13]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[CH:12]2)C1C=CC=CC=1>FC(F)(F)C(O)=O.O.CSC>[Cl:18][C:17]1[CH:16]=[C:15]2[C:11]([CH:12]=[C:13]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:14]2[CH2:19][C:20]2[N:25]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[CH:23]=[CH:22][CH:21]=2)=[CH:10][C:9]=1[OH:8]

참가 물질

3

반응물 1

HCID 69670868Methyl 6-(5-benzyloxy-6-chloro-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate

생성물 1

HCID 69670789Methyl 6-(6-chloro-5-hydroxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate수율 70.4%

시약·촉매·용매 1

HCID 86597598Trifluoroacetic acid water dimethylsulfide용매

실험 절차

A solution of methyl 6-(5-benzyloxy-6-chloro-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate (372 mg) in trifluoroacetic acid/water/dimethyl sulfide (95/5/10, 7.7 mL) was stirred at room temperature for 80 hours. The reaction mixture was concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution (20 mL) was added to the residue and this resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was triturated in dichloromethane/hexane (2/1). The precipitate was collected by filtration, washed with dichloromethane/hexane (2/1), and air-dried to obtain the title compound (213 mg).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionA saturated aqueous sodium hydrogen carbonate solution (20 mL) was added to the residue
  3. extractionthis resulting mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated in dichloromethane/hexane (2/1)
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with dichloromethane/hexane (2/1)
  9. customair-dried

출처 및 근거

ORD 기록
ord-64cfda7082ed4cbc97f34493cd22c7b8
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680120B2

반응 노트

불러오는 중…