Carbon tetrabromide → 7-Chloro-4-(2,2-dibromovinyl)-5-methyl-1-tosyl-1H-indole

HRID 2174048Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174048
[Cl:1][C:2]1[C:10]2[N:9]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:8]=[CH:7][C:6]=2[C:5]([CH:21]=O)=[C:4]([CH3:23])[CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:43](Br)(Br)([Br:45])[Br:44]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:23])[C:5]([CH:21]=[C:43]([Br:45])[Br:44])=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 72192144HCID 72192144, Verbindung

Produkt 1

HCID 867016717-Chloro-4-(2,2-dibromovinyl)-5-methyl-1-tosyl-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 7-chloro-5-methyl-1-tosyl-1H-indole-4-carbaldehyde (48 mg, 0.138 mmol) and PPh3 (109 mg, 0.414 mmol) in DCM (1.4 mL) at 0° C., was added CBr4 (68.6 mg, 0.207 mmol) and the reaction was warmed to room temperature. After 10 minutes the reaction mixture was loaded onto silica gel and was purified by flash chromatography (0-50% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.00 (d, J=3.79 Hz, 1H) 7.88 (s, 1H) 7.73 (m, J=8.59 Hz, 2H) 7.42 (m, J=7.83 Hz, 2H) 7.23 (s, 1H) 6.71 (d, J=3.79 Hz, 1H) 2.37 (s, 3H) 2.23 (s, 3H).

Aufarbeitung

  1. customwas purified by flash chromatography (0-50% EtOAc in heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-7d8fac92fc504c1bb117c29e9ba25792
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056874B2

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