N-Piperidinoethanol → tert-butyl 6-(2-(piperidin-1-yl)ethoxy)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

HRID 1677045노트

반응식

HRID 1677045 반응식
P([O-])([O-])([O-])=O.[K+].[K+].[K+].I[C:10]1[C:18]2[NH:17][C:16]3[CH2:19][CH2:20][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][C:15]=3[C:14]=2[CH:13]=[CH:12][CH:11]=1.[N:30]1([CH2:36][CH2:37][OH:38])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>C(Cl)Cl.[Cu]I>[N:30]1([CH2:36][CH2:37][O:38][C:10]2[C:18]3[NH:17][C:16]4[CH2:19][CH2:20][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][C:15]=4[C:14]=3[CH:13]=[CH:12][CH:11]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

참가 물질

6

반응물 3

HCID 18232N-PiperidinoethanolHCID 62657Potassium Phosphate, TribasicHCID 21952696tert-Butyl-6-iodo-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

생성물 1

HCID 57541278tert-butyl 6-(2-(piperidin-1-yl)ethoxy)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate수율 25%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6344Dichloromethane용매

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온도
150 °C

실험 절차

Tri-potassium orthophosphate (1.92 g, 9.04 mmol), tert-butyl 6-iodo-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (1.80 g, 4.52 mmol) and copper(I) iodide (0.430 g, 2.26 mmol) were suspended in 2-(piperidin-1-yl)ethanol (15 ml, large excess) and sealed into a microwave tube after bubbling argon through the solution for 5 minutes. The reaction was heated to 150° C. for 1.5 hours in the microwave reactor and cooled to RT. This reaction was repeat three times and the combined crude reaction mixture worked as follows. The mixture was diluted with DCM (50 mL) and washed with NaOH (3×30 mL), dried over sodium sulfate and the solvent removed under reduced pressure. The crude product was purified by preparative HPLC (0.1% HCOOH, CH3CN, H20). Fractions containing the desired compound were evaporated to dryness to afford tert-butyl 6-(2-(piperidin-1-yl)ethoxy)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (1.33 g, 25% yield) as a yellow gum.

후처리

  1. customsealed into a microwave tube
  2. customafter bubbling argon through the solution for 5 minutes
  3. temperaturecooled to RT
  4. customreaction mixture
  5. washwashed with NaOH (3×30 mL)
  6. dry with materialdried over sodium sulfate
  7. customthe solvent removed under reduced pressure
  8. customThe crude product was purified by preparative HPLC (0.1% HCOOH, CH3CN, H20)
  9. additionFractions containing the desired compound
  10. customwere evaporated to dryness

출처 및 근거

ORD 기록
ord-a3e09e131ee34bc28edf92c957386ffc
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008279B2

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