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Triethylamine → (1-acetyl-1H-indazol-5-yl)phosphonic Acid Dimethyl Ester

HRID 1726077
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1726077
[CH3:1][O:2][P:3]([O-:6])[O:4][CH3:5].C(N(CC)CC)C.[C:14]([N:17]1[C:25]2[C:20](=[CH:21][C:22](OS(C(F)(F)F)(=O)=O)=[CH:23][CH:24]=2)[CH:19]=[N:18]1)(=[O:16])[CH3:15]>CN(C)C=O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][P:3]([C:22]1[CH:21]=[C:20]2[C:25](=[CH:24][CH:23]=1)[N:17]([C:14](=[O:16])[CH3:15])[N:18]=[CH:19]2)(=[O:6])[O:4][CH3:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 21884954DimethylphosphiteHCID 57562419trifluoromethanesulfonic acid 1-acetyl-1H-indazol-5-yl ester

Produkt 1

HCID 57562465(1-acetyl-1H-indazol-5-yl)phosphonic Acid Dimethyl EsterAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

291 μl (1.09 eq; 3.172 mmol) of dimethylphosphite, 442 μl (1.09 eq; 3.172 mmol) of triethylamine and 134 mg (0.04 eq; 0.116 mmol) of tetrakis(triphenylphosphine)palladium(0) are stirred under an argon atmosphere for 15 minutes. 897 mg (1 eq; 2.91 mmol) of trifluoromethanesulfonic acid 1-acetyl-1H-indazol-5-yl ester in solution in 60 ml of dimethylformamide. The medium is heated at 105° C. for 4 hours under an argon atmosphere. The solvent is evaporated off under reduced pressure in a rotary evaporator, with 40 ml of toluene being added. The reaction crude is taken up in 40 ml of ethyl acetate and then washed with 50 ml of water. The organic phase is dried over magnesium sulfate and then filtered and the solvent is evaporated off under reduced pressure in a rotary evaporator. 973.6 mg of crude product are obtained. The reaction crude is purified by flash chromatography (silica 35-70 μm), eluent: ethyl acetate/cyclohexane 80:20 to obtain 430.5 mg of (1-acetyl-1H-indazol-5-yl)phosphonic acid dimethyl ester.

Aufarbeitung

  1. customThe solvent is evaporated off under reduced pressure in a rotary evaporator, with 40 ml of toluene being
  2. additionadded
  3. customThe reaction crude
  4. washwashed with 50 ml of water
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent is evaporated off under reduced pressure in a rotary evaporator
  8. custom973.6 mg of crude product are obtained
  9. customThe reaction crude
  10. customis purified by flash chromatography (silica 35-70 μm), eluent

Quellen und Nachweise

ORD-Eintrag
ord-ee35ea18e451418c875632cfed42ed03
Quelldatensatz
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07491710B2

Notizen zur Reaktion

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