Potassium Carbonate → 5-(5-{[{2-[(1,1-Dimethylethyl)oxy]ethyl}(methyl)amino]methyl}-3-thienyl)-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide

HRID 387330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387330
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][S:17](=[O:21])(=[O:20])[CH2:16][CH2:15]1.CC1(C)C(C)(C)OB([C:30]2[CH:31]=[C:32]([CH:35]=O)[S:33][CH:34]=2)O1.[C:38]([O-:41])([O-])=O.[K+].[K+]>O1CCOCC1.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>[CH3:5][C:14]([O:41][CH2:38][CH2:6][N:7]([CH2:35][C:32]1[S:33][CH:34]=[C:30]([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][S:17](=[O:21])(=[O:20])[CH2:16][CH2:15]2)[CH:31]=1)[CH3:8])([CH3:19])[CH3:15]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 467397834-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehydeHCID 593327575-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide

Produkt 1

HCID 593328005-(5-{[{2-[(1,1-Dimethylethyl)oxy]ethyl}(methyl)amino]methyl}-3-thienyl)-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamideAusbeute 5,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (400 mg, 1.08 mmol) in dioxane and water (4 mL/1 mL) was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarbaldehyde (462 mg, 1.94 mmol), Pd(PPh3)4 (100 mg) and K2CO3 (447 mg, 3.24 mmol). The reaction mixture was heated at 150° C. for 20 minutes by microwave irradiation. The organic phase was concentrated and redissolved in DMSO (10 mL). The resulting solution was split to eight. NaBH3CN (30 mg), ZnCl2 (30 mg) and -[(1,1-dimethylethyl)oxy]ethyl}methylamine (50 mg) were added. The mixture was heated at 100° C. for 30 minutes which was then filtered and purified by HPLC with TFA to afford the title compound (15 mg).

Aufarbeitung

  1. concentrationThe organic phase was concentrated
  2. dissolutionredissolved in DMSO (10 mL)
  3. customThe resulting solution was split to eight
  4. additionNaBH3CN (30 mg), ZnCl2 (30 mg) and -[(1,1-dimethylethyl)oxy]ethyl}methylamine (50 mg) were added
  5. temperatureThe mixture was heated at 100° C. for 30 minutes which
  6. filtrationwas then filtered
  7. custompurified by HPLC with TFA

Quellen und Nachweise

ORD-Eintrag
ord-f361bcc49e5a415fa6cc431b8ad76b37
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372875B2

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