Triethylamine → 5-bromo-3-[1-(ethanesulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

HRID 562016

반응식

HRID 562016 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[CH2:20]([S:22](Cl)(=[O:24])=[O:23])[CH3:21].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][N:17]([S:22]([CH2:20][CH3:21])(=[O:24])=[O:23])[CH2:16][CH2:15]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 113247225-bromo-3-(4-piperidinyl)-1H-indole-7-carboxamide

생성물 1

HCID 113844275-bromo-3-[1-(ethanesulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide수율 69%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To 5-bromo-3-(4-piperidinyl)-1H-indole-7-carboxamide (900 mg, 2.8 mmol) in CH2Cl2 (100 mL) at 0° C., ethanesulfonyl chloride (0.8 mg, 8.4 mmol) and triethylamine (1.6 mL, 11.2 mmol) were added. The reaction mixture was stirred at 0° C. for 30 min., after which time the mixture was partitioned between CH2Cl2 and water. The aqueous phase was extracted with CH2Cl2 (50 mL×2) and the combined organic phase dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by solid phase extraction on a 500 mg aminopropyl column (International Sorbent Technologies) eluting with chloroform (30 mL×2) and ethyl acetate (50 mL) to give 800 mg of the title compound (69%).

후처리

  1. customafter which time the mixture was partitioned between CH2Cl2 and water
  2. extractionThe aqueous phase was extracted with CH2Cl2 (50 mL×2)
  3. dry with materialthe combined organic phase dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by solid phase extraction on a 500 mg aminopropyl column (International Sorbent Technologies)
  6. washeluting with chloroform (30 mL×2) and ethyl acetate (50 mL)

출처 및 근거

ORD 기록
ord-41e4f48c8b504d7fb7ee1a3ba7e9bea4
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063071B2

연결된 노트

불러오는 중…