Potassium Carbonate → 5-[4-(1-Hydroxy-1-methylethyl)phenyl]-2-({6-[(2-hydroxy-2-methylpropoxy)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide

HRID 385851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 385851
[NH2:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([OH:19])([CH3:18])[CH3:17])=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].Br[C:21]1[N:26]=[C:25]([CH2:27][O:28][CH2:29][C:30]([CH3:33])([OH:32])[CH3:31])[CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CCO>[OH:19][C:16]([C:13]1[CH:14]=[CH:15][C:10]([C:4]2[S:3][C:2]([NH:1][C:21]3[CH:22]=[CH:23][CH:24]=[C:25]([CH2:27][O:28][CH2:29][C:30]([OH:32])([CH3:31])[CH3:33])[N:26]=3)=[C:6]([C:7]([NH2:9])=[O:8])[CH:5]=2)=[CH:11][CH:12]=1)([CH3:17])[CH3:18]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 583352721-[(6-Bromopyridin-2-yl)methoxy]-2-methylpropan-2-olHCID 595262122-Amino-5-[4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide

Produkt 1

HCID 595263105-[4-(1-Hydroxy-1-methylethyl)phenyl]-2-({6-[(2-hydroxy-2-methylpropoxy)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-Amino-5-[4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide (0.1 g, 0.362 mmol), 1-[(6-bromopyridin-2-yl)methoxy]-2-methylpropan-2-ol (Example 217 Step 1) (0.085 g, 0.326 mmol), Pd2dba3 (0.017 g, 0.018 mmol), K2CO3 (0.055 g, 0.398 mmol) and X-Phos (0.043 g, 0.090 mmol) were added to a 5 mL microwave vial. Degassed EtOH (1 mL) was added and the vial evacuated and back-filled with N2 (3×). The resulting mixture was stirred at 100° C. overnight. After cooling to room temperature, the mixture was diluted with methanol, silica gel was added, and the solvent was removed in vacuo. Purification of the residue by flash chromatography (silica, 0-10% MeOH—CHCl3) gave the title compound as a beige solid after triturating in EtOAc.

Aufarbeitung

  1. customthe vial evacuated
  2. additionback-filled with N2 (3×)
  3. temperatureAfter cooling to room temperature
  4. additionthe mixture was diluted with methanol, silica gel
  5. additionwas added
  6. customthe solvent was removed in vacuo
  7. customPurification of the residue by flash chromatography (silica, 0-10% MeOH—CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-1e0f0d0bc25a4bd48dbce20ad2bd3778
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

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