Acetic Acid → 5-(4-Fluoro-phenyl)-3-isopropylamino-thiophene-2-carboxylic acid methyl ester

HRID 73200

Reaktionsgleichung

Reaktionsgleichung von HRID 73200
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH2:10])=[O:4].CO[C:20]([CH3:22])=[CH2:21].CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.CCOC(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH:10][CH:20]([CH3:22])[CH3:21])=[O:4]

Komponenten

9

Edukt 5

HCID 176Acetic AcidHCID 83002-MethoxypropeneHCID 516892Sodium BicarbonateHCID 619692Methyl 3-amino-5-(4-fluorophenyl)thiophene-2-carboxylateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 597523015-(4-Fluoro-phenyl)-3-isopropylamino-thiophene-2-carboxylic acid methyl esterAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-amino-5-(4-fluoro-phenyl)-thiophene-2-carboxylic acid methyl ester (0.502 g, 2.0 mmol) in 1,2-dichloroethane (6.0 mL) was added sequentially 2-methoxypropene (0.38 mL, 4.0 mmol), AcOH (0.114 mL, 2.0 mmol) and NaBH(OAc)3 (0.84 g, 4.0 mmol) and stirred for 2 hrs. It was then diluted with EtOAc and H2O. The aqueous solution was adjusted to pH=7 by adding NaHCO3. The aqueous phase was extracted with EtOAc, the combined extract was washed with brine and dried on MgSO4 and filtered. Purification on bond elute with hexane to 10% EtOAc-hexane furnished 5-(4-fluoro-phenyl)-3-isopropylamino thiophene-2-carboxylic acid methyl ester (0.538 g, 92% yield).

Aufarbeitung

  1. extractionThe aqueous phase was extracted with EtOAc
  2. extractionthe combined extract
  3. washwas washed with brine
  4. customdried on MgSO4
  5. filtrationfiltered
  6. customPurification on bond
  7. washelute with hexane to 10% EtOAc-hexane

Quellen und Nachweise

ORD-Eintrag
ord-789741ea3aa34225b983f7c28de2ee9b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829030B2

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