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

HRID 73165

Reaktionsgleichung

Reaktionsgleichung von HRID 73165
[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 91 %

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 (500 mg, 2.0 mmol) in 1,2-dichloroethane (10 mL) was added sequentially 2-methoxypropene (0.76 mL, 8.0 mmol), AcOH (0.12 mL, 4.0 mmol) and NaBH(OAc)3 (0.848 mg, 8.0 mmol) and stirred for 16 h. 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 5% EtOAc-hexane furnished 5-(4-Fluoro-phenyl)-3-isopropylamino-thiophene-2-carboxylic acid methyl ester (0.530 mg, 91% yield). 1H NMR (CDCl3, 400 MHz): δ 7.62 (d, 2H), 7.09 (m, 2H), 6.81 (s, 1H), 3.84 (s, 3H), 3.71 (m, 1H), 1.35 (d, 6H).

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 5% EtOAc-hexane

Quellen und Nachweise

ORD-Eintrag
ord-5bd717609296450abc7645a50104cf74
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829030B2

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