Triphenylphosphine → 2-[1-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)cyclopropyI]ethyl bromide

HRID 1683977

Reaktionsgleichung

[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:22][C:23]1[CH:47]=[CH:46][C:26]([CH2:27][N:28]2[C:36]3[C:31](=[CH:32][C:33]([O:37][CH3:38])=[CH:34][CH:35]=3)[C:30]([C:39]3([CH2:42][CH2:43]O)[CH2:41][CH2:40]3)=[C:29]2[CH3:45])=[CH:25][CH:24]=1>C(Cl)Cl>[Br:22][C:23]1[CH:47]=[CH:46][C:26]([CH2:27][N:28]2[C:36]3[C:31](=[CH:32][C:33]([O:37][CH3:38])=[CH:34][CH:35]=3)[C:30]([C:39]3([CH2:42][CH2:43][Br:1])[CH2:41][CH2:40]3)=[C:29]2[CH3:45])=[CH:25][CH:24]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Bromine (136 mg, 0.85 mmol) was added to a-78° C. solution of triphenylphosphine (244 rag, 0.93 mmol) in 4 mL CH2Cl2, and the mixture was stirred 0.5 h at 0° C. and 5 rain at r.t. before recooling to -5° C. The alcohol from Step 8 (319 mg, 0.77 mmol) was then slowly added as a 1 mL CH2Cl2 solution and the mixture was stirred 2 h at 0° C. The reaction mixture was partitioned between CH2Cl2 and saturated NaHCO3. The organic layer was dried over MgSO4, concentrated and the residue purified by flash chromatography (10% ethyl acetate in hexane) to give 166 mg of the title compound.

Aufarbeitung

customat r.t.
custombefore recooling to -5° C
stirringthe mixture was stirred 2 h at 0° C
customThe reaction mixture was partitioned between CH2Cl2 and saturated NaHCO3
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated
customthe residue purified by flash chromatography (10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag: ord-daf665c75ff14761a40045b1545ca78c
Quelldatensatz: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05639780

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