Triethylamine → HCID 10168896, Verbindung

HRID 352990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 352990
[OH:1][CH:2]([C:5]1[CH:10]=[C:9]([I:11])[N:8]([CH2:12][C:13]#[CH:14])[C:7](=[O:15])[C:6]=1[CH3:16])[CH2:3][CH3:4].CCN(CC)CC.Br[Si:25]([CH:44]([CH3:46])[CH3:45])([CH:41]([CH3:43])[CH3:42])[CH2:26][CH2:27][C:28]([F:40])([F:39])[C:29]([F:38])([F:37])[C:30]([F:36])([F:35])[C:31]([F:34])([F:33])[F:32]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:44]([Si:25]([CH:41]([CH3:43])[CH3:42])([CH2:26][CH2:27][C:28]([F:40])([F:39])[C:29]([F:37])([F:38])[C:30]([F:35])([F:36])[C:31]([F:32])([F:33])[F:34])[O:1][CH:2]([C:5]1[CH:10]=[C:9]([I:11])[N:8]([CH2:12][C:13]#[CH:14])[C:7](=[O:15])[C:6]=1[CH3:16])[CH2:3][CH3:4])([CH3:45])[CH3:46]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 22706711HCID 22706711, VerbindungHCID 86594466HCID 86594466, Verbindung

Produkt 1

HCID 10168896HCID 10168896, VerbindungAusbeute 83,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(1-hydroxypropyl)-6-iodo-3-methyl-1-prop-2-ynyl-1H-pyridin-2-one 4b (44 mg, 0.13 mmol) and 4-dimethylaminopyridine (2 mg, 1.2 μmol) in CH2Cl2 (2 mL) was added NEt3 (53 mg, 74 μL, 0.52 mmol) and bromodiisopropyl(3, 3, 4, 4, 5, 5, 6, 6, 6-nonafluorohexyl)silane (147 mg, 0.33 mmol, prepared by mixing diisopropyl-(3, 3, 4, 4, 5, 5, 6, 6, 6-nonafluorohexyl)silane and Br2) and the mixture was stirred for 12 h. The solvent was evaporated and the residue was purified by flash chromatography (hexanes-EtOAc 15:1) to afford 5b (75 mg, 82%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ6.99 (s, 1H), 5.12 (d, J=16.5, 1H), 5.00 (d, J=16.5, 1H), 4.75 (t, J=6.0 Hz, 1H), 2.33-2.31 (m, 1H), 2.07-1.99 (m, 2H) 2.06 (s, 3H), 1.84-1.60 (m, 2H), 1.00 (s, 14H), 0.88 (t, J=7.4 Hz, 3H), 0.83-0.79 (m, 2H); 13C NMR (75 MHz, CDCl3) δ162.4, 152.5, 123.7, 118.6, 94.2, 72.8, 71.5, 44.3, 31.1, 25.3, 17.5, 12.6, 9.4, 0.3.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography (hexanes-EtOAc 15:1)

Quellen und Nachweise

ORD-Eintrag
ord-8fc7d8718346437bb4a5ce56c6cb3a8f
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06749756B1

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