Cesium carbonate → 5-(5-formyl-3-thienyl)-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide

HRID 1806219

Reaktionsgleichung

Reaktionsgleichung von HRID 1806219
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][N:17]([S:20]([CH:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])[CH2:16][CH2:15]1.CC1(C)C(C)(C)OB([C:34]2[CH:35]=[C:36]([CH:39]=[O:40])[S:37][CH:38]=2)O1.C([O-])([O-])=O.[Cs+].[Cs+]>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>[CH:39]([C:36]1[S:37][CH:38]=[C:34]([C:2]2[CH:3]=[C:4]3[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=2)[NH:7][CH:6]=[C:5]3[CH:14]2[CH2:19][CH2:18][N:17]([S:20]([CH:23]([CH3:25])[CH3:24])(=[O:21])=[O:22])[CH2:16][CH2:15]2)[CH:35]=1)=[O:40]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 467397834-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehydeHCID 577326275-bromo-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide

Produkt 1

HCID 577327835-(5-formyl-3-thienyl)-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamideAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, VerbindungKatalysator

Versuchsvorschrift

A solution of 5-bromo-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide (428 mg, 1 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarbaldehyde (960 mg, 4 mmol), Cs2CO3 (800 mg, 2.46 mmol), and Pd(PPh3)4 (100 mg, 0.0865 mmol) were heated in a Smith microwave at 160° C. for 20 min. The reaction mixture was filtered and concentrated under reduced pressure. The crude product was washed with MeOH (1×5 mL) to give the title compound (395 mg, 86%).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. washThe crude product was washed with MeOH (1×5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-ff074b376a784b24aa484ca3326a5548
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354406B2

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