Triethylamine → HCID 22961811, Verbindung

HRID 365865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 365865
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19](Br)[CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:22]#[C:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].CCN(CC)CC>C(Cl)Cl.[Cu]I>[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:22]#[C:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 123701-OctyneHCID 154802363-bromo-5-[[1-(tert-butoxycarbonyl)-2(R)-pyrrolidinyl]methoxy]pyridine

Produkt 1

HCID 22961811HCID 22961811, VerbindungAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-(1-BOC-2-(R)-pyrrolidinylmethoxy)-5-bromopyridine (300 mg, 0.84 mmol), 1-octyne (0.2 mL, 1.4 mmol), Pd(PPh)3Cl2 (12 mg), CuI (catalytic amount) and NEt3 (2.45 mL) in CH2Cl2 (7 mL) was heated at reflux for 16 h. The solvent was removed, and the residue was washed with 10% NaOH then extracted with CH2Cl2. The organic extract was dried (MgSO4) and concentrated. The residue was chromatographed (silica gel; CHCl3 /MeOH, 10:1) to afford the title compound (302 mg) that contaminated with starting material.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. customThe solvent was removed
  4. washthe residue was washed with 10% NaOH
  5. extractionthen extracted with CH2Cl2
  6. extractionThe organic extract
  7. dry with materialwas dried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was chromatographed (silica gel; CHCl3 /MeOH, 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-e933e457ec6d4cb88b828f7b7511e3bd
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127386

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