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

HRID 1896517

反応式

HRID 1896517 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3fac0b86374e4f22b38c2e6e188545ea
出典データセット
uspto-grants-2013_08
特許番号
US08518964B2

関連ノート

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