Dichloromethane → 5-(Pyrid-3-yl)-3-(1-Methylpiperidin-4-yl)-1H-Indole

HRID 278015노트

반응식

HRID 278015 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](B(O)O)[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.Br[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1.ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C.[OH-].[Na+]>[N:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[NH:10][CH:9]=[C:8]3[CH:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:22]=1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 122863-BromopyridineHCID 120418133-(1-Methylpiperidin-4-yl)-1H-Indole-5-Boronic Acid

생성물 1

HCID 99041215-(Pyrid-3-yl)-3-(1-Methylpiperidin-4-yl)-1H-Indole수율 53%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매

실험 절차

A mixture of 3-(1-methylpiperidin-4-yl)-1H-indole-5-boronic acid (0.200g, 0.78 mmol), 3-bromopyridine (0.117 g, 0.74 mmol), 1,1′-[bis(diphenylphosphino)ferrocene]-dichloropalladium(II) complex with dichloromethane (Pd(dppf)Cl2.CH2Cl2) (0.03 g, 0.37 mmol), and 2M aqueous sodium carbonate solution (2 mL) in 7 mL of tetrahydrofuran was heated at reflux, with stirring, overnight. The mixture was allowed to cool to room temperature, diluted with ethyl acetate and 2N aqueous sodium hydroxide solution, and the organic phase was separated, washed with brine solution, dried over sodium sulfate, concentrated in vacuo and purified by silica gel (flash) chromatography (solvent gradient: 100% dichloromethane—25:2 dichloromethane: methanol/aqueous ammonium hydroxide) to give 0.114 g (53%) of the title compound as an amorphous pink solid. FDMS m/e=291 (M+). EA calculated for C19H21N3: C, 78.32; H, 7.26; N, 14.42. Found: C, 78.39; H, 7.39; N, 14.36.

후처리

  1. temperaturewas heated
  2. temperatureat reflux
  3. customthe organic phase was separated
  4. washwashed with brine solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel (flash) chromatography (solvent gradient: 100% dichloromethane—25:2 dichloromethane: methanol/aqueous ammonium hydroxide)

출처 및 근거

ORD 기록
ord-9a97e1b955034872b61dd8386705cd20
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06358972B1

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