Potassium Acetate → 5-(5-(Cyclopropylcarbamoyl)-2-methylphenylcarbamoyl)thiophen-2-ylboronic acid

HRID 544946

Reaktionsgleichung

Reaktionsgleichung von HRID 544946
ClC1C=CC=CC=1[C:8]1[CH:12]=[CH:11][S:10][C:9]=1[C:13]([NH:15][C:16]1[CH:21]=[C:20]([C:22](=[O:27])[NH:23][CH:24]2[CH2:26][CH2:25]2)[CH:19]=[CH:18][C:17]=1[CH3:28])=[O:14].[B:29]1(B2OC(C)(C)C(C)(C)O2)[O:33]C(C)(C)C(C)(C)[O:30]1.CC([O-])=O.[K+]>CN(C=O)C>[CH:24]1([NH:23][C:22]([C:20]2[CH:19]=[CH:18][C:17]([CH3:28])=[C:16]([NH:15][C:13]([C:9]3[S:10][C:11]([B:29]([OH:33])[OH:30])=[CH:12][CH:8]=3)=[O:14])[CH:21]=2)=[O:27])[CH2:26][CH2:25]1

Komponenten

5

Edukt 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 67148792(2-Chlorophenyl)-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)thiophene-2-carboxamide

Produkt 1

HCID 597615035-(5-(Cyclopropylcarbamoyl)-2-methylphenylcarbamoyl)thiophen-2-ylboronic acidAusbeute 178,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of 1.0 g (2.64 mmol) of 5-bromo-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)thiophene-2-carboxamide (Example 136, Step B), bis(pinacolato)diborane (1.0 g, 3.95 mmol) and KOAc (1.30 g, 13.2 mmol) in DMF (15 mL) was purged with argon and Pd(dppf)2Cl2/CH2Cl2 complex (65 mg, 0.08 mmol) was added followed by heating at 90° C. for 16 h. After cooling to rt, the mixture was partitioned between EtOAc (250 mL) and water (50 mL) and the layers were separated. The organic portion was washed with additional water, then brine, then dried over anhyd Na2SO4, filtered, and concentrated under vacuum to afford 1.62 g of a brown semi-solid as the crude product mixture. This material was triturated with EtOAc and filtered to afford 626 mg of the compound a containing ˜10% of the boronate ester. This material was used as is without any further purification. HPLC Ret time=2.36 min. LCMS [M+H]+ 345.2.

Aufarbeitung

  1. additionwas added
  2. temperatureAfter cooling to rt
  3. customthe mixture was partitioned between EtOAc (250 mL) and water (50 mL)
  4. customthe layers were separated
  5. washThe organic portion was washed with additional water
  6. dry with materialbrine, then dried over anhyd Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-135ecc26917e4d76af946caa32bbb78a
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935696B2

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