3-Butyn-1-OL → HCID 491972, 화합물

HRID 1841540노트

반응식

HRID 1841540 반응식
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:15][C:14]=3I)=[O:9])=[CH:4][CH:3]=1.[CH2:31]([OH:35])[CH2:32][C:33]#[CH:34]>N(CC)CC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13]4=[C:14]([CH:34]=[C:33]([CH2:32][CH2:31][OH:35])[N:12]4[CH:11]=2)[CH:15]=[C:16]([CH2:21][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:17]=3)=[O:9])=[CH:4][CH:3]=1

참가 물질

6

반응물 2

HCID 135663-Butyn-1-OLHCID 178522927HCID 178522927, 화합물

생성물 1

HCID 491972HCID 491972, 화합물수율 71%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8021Diethylamine용매

실험 절차

A solution of N-(4-chlorobenzyl)-4-hydroxy-8-iodo-6-(tetrahydro-2H-pyran-4-ylmethyl)-3-quinolinecarboxamide (0.16 g), PdCl2(PPh3)2, CuI (0.018 g) and 3-butyn-1-ol (0.03 mL) in 15 mL Et2NH is stirred at room temperature for 7 days. The solid in the reaction is filtered and rinsed with EtOAc. The filtrate is partitioned between EtOAc and H2O. The aqueous layer is extracted with EtOAc (3×). The organic layers and the solid previously filtered are combined, concentrated, adsorbed onto silica and chromatographed (gradient from CH2Cl2 to 4% MeOH in CH2Cl2). Product-containing fractions are combined and condensed to afford 101.6 mg (71%) of N-(4-chlorobenzyl)-2-(2-hydroxyethyl)-6-oxo-8-(tetrahydro-2H-pyran-4-ylmethyl)-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide as a tan solid.

후처리

  1. filtrationThe solid in the reaction is filtered
  2. washrinsed with EtOAc
  3. customThe filtrate is partitioned between EtOAc and H2O
  4. extractionThe aqueous layer is extracted with EtOAc (3×)
  5. filtrationThe organic layers and the solid previously filtered
  6. concentrationconcentrated
  7. customchromatographed (gradient from CH2Cl2 to 4% MeOH in CH2Cl2)
  8. customcondensed

출처 및 근거

ORD 기록
ord-d0a5427a349f432d86821072c7f1f785
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06683181B2

반응 노트

불러오는 중…