Dichloromethane → 4-cyano-5-ethyl-1-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 1865054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1865054
[CH3:1][C:2]1([CH3:9])[C:6]([CH3:8])([CH3:7])[O:5][BH:4][O:3]1.[CH2:10]([O:12][C:13]([C:15]1[N:16]([CH3:25])[C:17]([CH2:23][CH3:24])=[C:18]([C:21]#[N:22])[C:19]=1I)=[O:14])[CH3:11].C(Cl)Cl.C(N(CC)CC)C>C(#N)C.O>[CH2:10]([O:12][C:13]([C:15]1[N:16]([CH3:25])[C:17]([CH2:23][CH3:24])=[C:18]([C:21]#[N:22])[C:19]=1[B:4]1[O:5][C:6]([CH3:8])([CH3:7])[C:2]([CH3:9])([CH3:1])[O:3]1)=[O:14])[CH3:11]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 57975348HCID 57975348, Verbindung

Produkt 1

HCID 579748024-cyano-5-ethyl-1-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Add 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.87 mL, 6.0 mmol) to 4-cyano-5-ethyl-3-iodo-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.0 g, 3.0 mmol, prepared in prepared in Preparation 38), [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) complex with methylene chloride (1:1) (0.122 g, 0.15 mmol), and triethylamine (1.25 mL, 9.0 mmol) in acetonitrile and heat to reflux. After 3 hours, cool and pour into water. Extract with ethyl acetate. Wash the combined organics with water and brine, dry over magnesium sulfate, filter and concentrate under reduced pressure. Purify the residue by flash chromatography (silica gel), eluting with ethyl acetate:hexanes to provide the title compound. 1H NMR (400 MHz, CDCl3) δ 4.33 (q, 2H), 3.84 (s, 3H), 2.80 (q, 2H), 1.40 (s, 12H), 1.46 (t, 3H), 1.22 (t, 3H).

Aufarbeitung

  1. temperatureheat to reflux
  2. temperaturecool
  3. extractionExtract with ethyl acetate
  4. washWash the combined organics with water and brine
  5. dry with materialdry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify the residue by flash chromatography (silica gel)
  9. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5f4c73361e964e13987ed25e8e5423eb
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625932B2

Notizen zur Reaktion

Wird geladen…