Potassium Carbonate → 1-(5-{(S)-1-[(R)-1-(4-Methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-3-yl)-1H-indole-4-carboxylic acid ethyl ester

HRID 880609노트

반응식

HRID 880609 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C@@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C@@H:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])[CH:7]=1.[CH2:23]([O:25][C:26]([C:28]1[C:29]2[CH:30]=[CH:31][NH:32][C:33]=2[CH:34]=[CH:35][CH:36]=1)=[O:27])[CH3:24].C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1.[Cu](I)I>[CH2:23]([O:25][C:26]([C:28]1[C:29]2[CH:30]=[CH:31][N:32]([C:2]3[CH:3]=[N:4][CH:5]=[C:6]([C@@H:8]4[CH2:12][CH2:11][CH2:10][N:9]4[C@@H:13]([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=4)[CH3:14])[CH:7]=3)[C:33]=2[CH:34]=[CH:35][CH:36]=1)=[O:27])[CH3:24]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 605034Ethyl indole-4-carboxylateHCID 581118453-Bromo-5-{(S)-1-[(R)-1-(4-methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridine

생성물 1

HCID 679743931-(5-{(S)-1-[(R)-1-(4-Methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-3-yl)-1H-indole-4-carboxylic acid ethyl ester수율 42.6%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
190 °C

실험 절차

A mixture of 3-bromo-5-{(S)-1-[(R)-1-(4-methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridine (4.0 g, 11 mmol), 1H-indole-4-carboxylic acid ethyl ester (6.3 g, 33 mmol), K2CO3 (2.3 g, 16.6 mmol), copper iodide (0.42 g, 2.2 mmol) in NMP (22 mL) was heated in a microwave tube at 190° C. for 30 minutes. The resulting mixture was cooled to room temperature filtered through celite and concentrated under reduced pressure to give an oil. This oil was purified by silica gel column chromatography (30% ethyl acetate/heptane) to give the titled compound as a yellow solid (2.2 g, 42%).

후처리

  1. temperatureThe resulting mixture was cooled to room temperature
  2. filtrationfiltered through celite and
  3. concentrationconcentrated under reduced pressure
  4. customto give an oil
  5. customThis oil was purified by silica gel column chromatography (30% ethyl acetate/heptane)

출처 및 근거

ORD 기록
ord-7f13e24fa1d344e0817a7cd5b9bcff6d
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993523B2

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