Ethanol → (2-Chlorophenyl)-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)thiophene-2-carboxamide

HRID 544927

Reaktionsgleichung

Reaktionsgleichung von HRID 544927
Br[C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[CH:15]=[C:14]([C:16](=[O:21])[NH:17][CH:18]3[CH2:20][CH2:19]3)[CH:13]=[CH:12][C:11]=2[CH3:22])=[O:8])=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.C(O)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CCOC(C)=O.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>[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:4]1[CH:3]=[CH:2][S:6][C:5]=1[C:7]([NH:9][C:10]1[CH:15]=[C:14]([C:16](=[O:21])[NH:17][CH:18]2[CH2:20][CH2:19]2)[CH:13]=[CH:12][C:11]=1[CH3:22])=[O:8]

Komponenten

8

Edukt 4

HCID 702EthanolHCID 62657Potassium Phosphate, TribasicHCID 27343222-Chlorophenylboronic acidHCID 597614015-Bromo-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)thiophene-2-carboxamide

Produkt 1

HCID 67148792(2-Chlorophenyl)-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)thiophene-2-carboxamideAusbeute 64,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

5-Bromo-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)thiophene-2-carboxamide (80 mg, 0.21 mmol) and 2-chlorophenylboronic acid (50 mg, 0.32 mmol) in toluene (0.7 mL) was purged with argon and ethanol (0.14 mL), 2 M aq. K3PO4 (0.21 mL, 0.42 mmol), and Pd(PPh3)4 (12 mg, 0.010 mmol) was added. The resulting mixture was heated at 115° C. for 2 h. After cooling to rt, the mixture was diluted with EtOAc (100 mL), washed with brine and dried over anyhd. sodium sulfate. The solution was filtered and concentrated under vacuum to afford a yellow solid which was triturated with MeOH (2 mL), filtered to collect the solid and rinsed with additional MeOH (2×0.5 mL) and dried under vacuum to afford 56 mg of a white solid as the title compound (Example 136). HPLC Ret time=3.56 min. LCMS [M+H]+ 411.21.

Aufarbeitung

  1. additionwas added
  2. temperatureAfter cooling to rt
  3. washwashed with brine
  4. customdried over anyhd
  5. filtrationThe solution was filtered
  6. concentrationconcentrated under vacuum
  7. customto afford a yellow solid which
  8. customwas triturated with MeOH (2 mL)
  9. filtrationfiltered
  10. customto collect the solid
  11. washrinsed with additional MeOH (2×0.5 mL)
  12. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-853c6265e22d4ecba748bcb7a823bd8d
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935696B2

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