Dichloromethane → HCID 178519325, Verbindung

HRID 707466

Reaktionsgleichung

Reaktionsgleichung von HRID 707466
Br[C:2]1[CH:3]=[C:4]([CH:10]=[O:11])[S:5][C:6]=1[N+:7]([O-:9])=[O:8].[NH:12]1[C:16](B(O)O)=[CH:15][CH:14]=[N:13]1.COCCOC.ClCCl>C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O.C(N(CC)CC)C>[N+:7]([C:6]1[S:5][C:4]([CH:10]=[O:11])=[CH:3][C:2]=1[C:16]1[CH:15]=[CH:14][NH:13][N:12]=1)([O-:9])=[O:8]

Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 80711,2-DimethoxyethaneHCID 112519791H-Pyrazole-5-boronic acidHCID 218862814-Bromo-5-nitrothiophene-2-carbaldehyde

Produkt 1

HCID 178519325HCID 178519325, VerbindungAusbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A flask containing 4-bromo-5-nitrothiophene-2-carbaldehyde (1.00 g, 4.24 mmol), (1H-pyrazol-5-yl)boronic acid (510 mg, 4.56 mmol), ethyleneglycol dimethyl ether (20 mL), triethylamine (1.80 mL), water (2.00 mL) and bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (340 mg, 0.42 mmol) was evacuated and purged with nitrogen twice, then heated at 80° C. under nitrogen for 4 h. The reaction was cooled to room temperature, poured into a saturated solution of ammonium chloride (20 mL), extracted with ethyl acetate (3×10 mL), combined organics washed with a saturated solution of ammonium chloride (30 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography, eluting with ethyl acetate in hexanes, to yield 5-nitro-4-(1H-pyrazol-3-yl)thiophene-2-carbaldehyde as a yellow oil (950 mg, 28%). 1H NMR (400 MHZ, DMSO-d6) δ 6.99 (s, 1H), 7.94 (s, 1H), 8.42 (s, 1H), 10.07 (s, 1H).

Aufarbeitung

  1. customwas evacuated
  2. custompurged with nitrogen twice
  3. temperatureThe reaction was cooled to room temperature
  4. additionpoured into a saturated solution of ammonium chloride (20 mL)
  5. extractionextracted with ethyl acetate (3×10 mL)
  6. washcombined organics washed with a saturated solution of ammonium chloride (30 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by flash chromatography
  10. washeluting with ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ceebab437e3f454a9bd99cf7b5456914
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09175010B2

Verknüpfte Notizen

Wird geladen…