Sodium Carbonate → 1H-Indole-6-carboxamide

HRID 1982865

Reaktionsgleichung

Reaktionsgleichung von HRID 1982865
Br[C:2]1[NH:3][C:4]2[C:9]([C:10]=1C1CCCCC1)=[CH:8][CH:7]=[C:6]([C:17]([NH:19]S(N(C)C)(=O)=O)=[O:18])[CH:5]=2.COC1C=CC(B(O)O)=C(C=O)C=1.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>CCO.C1(C)C=CC=CC=1.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>[NH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:17]([NH2:19])=[O:18])[CH:5]=2)[CH:10]=[CH:2]1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27343652-Formyl-4-methoxybenzeneboronic acidHCID 587651502-bromo-3-cyclohexyl-N-(dimethylsulfamoyl)-1H-indole-6-carboxamide

Produkt 1

HCID 5948371H-Indole-6-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 21863594Toluene ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a slurried solution of 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]-indole-6-carboxamide (54.0 g, 126 mmol), 4-methoxy-2-formylphenylboronic acid (29.5 g, 164 mmol) and LiCl (13.3 g, 315 mmol) in EtOH/toluene (1:1, 1 L) was added a solution of Na2CO3 (40.1 g, 379 mmol) in water (380 mL). The reaction mixture was stirred 10 min. and then Pd(PPh3)4 (11.3 g, 10.0 mmol) was added. The reaction solution was flushed with nitrogen and heated at 70° C. (internal monitoring) overnight and then cooled to rt. The reaction was diluted with EtOAc (1 L) and EtOH (100 mL), washed carefully with 1N aqueous HCl (1 L) and brine (500 mL), dried (MgSO4), filtered and concentrated. The residual solids were stirred with Et2O (600 mL) for 1 h and collected by filtration to yield 1H-indole-6-carboxamide, 3-cyclohexyl-N-[(dimethylamino)sulfonyl]-2-(2-formyl-4-methoxyphenyl)- (52.8 g, 109 mmol, 87%) as a yellow powder which was used without further purification.

Aufarbeitung

  1. customThe reaction solution was flushed with nitrogen
  2. temperaturecooled to rt
  3. additionThe reaction was diluted with EtOAc (1 L) and EtOH (100 mL)
  4. washwashed carefully with 1N aqueous HCl (1 L) and brine (500 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. stirringThe residual solids were stirred with Et2O (600 mL) for 1 h
  9. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-fe2a5a335db24892a48e6c367619da06
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07541353B2

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