Potassium Carbonate → Methyl 7-(4-carbamoylphenoxy)-6-cyanochroman-4-carboxylate
Reaktionsgleichung
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1F)[O:9][CH2:8][CH2:7][CH:6]2[C:14]([O:16][CH3:17])=[O:15])#[N:2].[OH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH2:25])=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[C:23]([C:22]1[CH:26]=[CH:27][C:19]([O:18][C:12]2[CH:11]=[C:10]3[C:5]([CH:6]([C:14]([O:16][CH3:17])=[O:15])[CH2:7][CH2:8][O:9]3)=[CH:4][C:3]=2[C:1]#[N:2])=[CH:20][CH:21]=1)(=[O:24])[NH2:25]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 110 °C
Versuchsvorschrift
Methyl 6-cyano-7-fluorochroman-4-carboxylate (300 mg, 1.28 mmol), 4-hydroxybenzamide (227 mg, 1.66 mmol) and potassium carbonate (423 mg, 3.06 mmol) were diluted with dry NMP (4 mL). The reaction was bubbled with argon for 10 minutes and then heated at 110° C. for 12 hours. The reaction was cooled and loaded directly onto a biotage 40M cartridge (silica gel), eluting with 5% ethyl acetate/hexanes to 100% ethyl acetate to yield methyl 7-(4-carbamoylphenoxy)-6-cyanochroman-4-carboxylate (100 mg, 22.3% yield).
Aufarbeitung
- customThe reaction was bubbled with argon for 10 minutes
- temperatureThe reaction was cooled
- washeluting with 5% ethyl acetate/hexanes to 100% ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-60920c21c31b4508809d18b0c1b05bc0
- Quelldatensatz
- uspto-grants-2014_07
- Patentnummer
- US08785445B2
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