Hydrochloric Acid → tert-Butyl (5-methyl-1-tosyl-1H-indol-4-yl)carbamate

HRID 2174044Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174044
Br[C:2]1[C:3]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[CH:5]2.[CH3:29][B-](F)(F)F.[K+].C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+].Cl>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:29][C:2]1[C:3]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:15]=[CH:16][C:17]([CH3:18])=[CH:19][CH:20]=1)(=[O:12])=[O:13])[CH:6]=[CH:5]2

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 23692566Potassium Trifluoro(methyl)borateHCID 86701667tert-butyl (5-bromo-1-tosyl-1H-indol-4-yl)carbamate

Produkt 1

HCID 86701666tert-Butyl (5-methyl-1-tosyl-1H-indol-4-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (5-bromo-1-tosyl-1H-indol-4-yl)carbamate (9.95 g, 21.38 mmol) in toluene (194 mL) was added potassium methyltrifluoroborate (13 g, 107 mmol) and PdCl2(dppf).CH2Cl2 adduct (1.75 g, 2.138 mmol) and Cs2CO3 (20.90 g, 64.1 mmol) and finally water (19.44 mL), and the mixture was stirred at 100° C. After stirring overnight the reaction was cooled to room temperature and 1N HCl (100 mL) was added. The layers were separated and the aqueous layer was extracted with EtOAc, washed with 1N HCl, dried over MgSO4, filtered and concentrated to provide the title compound, which was used in the next reaction without any further purification. MS (ESI−) m/z 399.2 (M−H).

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washwashed with 1N HCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c89fafe4fc8b42f2b602653823b23ae2
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056874B2

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