methyl 1-chloro-5H-pyrido[4,3-b]indole-4-carboxylate → 1-chloro-5H-pyrido[4,3-b]indole-4-carboxamide

HRID 1896517

반응식

HRID 1896517 반응식
[Cl:1][C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[C:5]([C:15]([O:17]C)=O)=[CH:4][N:3]=1.[Li][NH2:20]>C1COCC1>[Cl:1][C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[C:5]([C:15]([NH2:20])=[O:17])=[CH:4][N:3]=1

참가 물질

4

반응물 2

HCID 59198422methyl 1-chloro-5H-pyrido[4,3-b]indole-4-carboxylateHCID 178506930HCID 178506930, 화합물

생성물 1

HCID 591984571-chloro-5H-pyrido[4,3-b]indole-4-carboxamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
100 °C

실험 절차

A mixture containing methyl 1-chloro-5H-pyrido[4,3-b]indole-4-carboxylate and LiNH2 (prepared in situ from ammonia and n-BuLi; 1.0 M in THF; 3.5 equiv) in THF (0.09 M) was heated in a microwave reactor at 100° C. for 1 min in a sealed tube. The reaction mixture was cooled to room temperature and partitioned between EtOAc and saturated NaHCO3. After separation of the organic phase, the aqueous phase was extracted again with EtOAc, and the combined organic phases were washed with brine, dried over MgSO4 and filtered. After evaporation of the organic solvent, the residue was purified by flash chromatography (10-70% EtOAc in hexanes) to provide the title compound as a white solid.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between EtOAc and saturated NaHCO3
  3. customAfter separation of the organic phase
  4. extractionthe aqueous phase was extracted again with EtOAc
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customAfter evaporation of the organic solvent
  9. customthe residue was purified by flash chromatography (10-70% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-3fac0b86374e4f22b38c2e6e188545ea
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518964B2

연결된 노트

불러오는 중…