Triphenylphosphine → 1-(6,7-Di-vinyl-2-benzothiazolyl)-3-ethylurea

HRID 9124

Reaktionsgleichung

Br[C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[C:3]=1S(C(F)(F)F)(=O)=O.[Cl-].[Li+].[C:26]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:27]=1.[CH:45]([Sn](C=C)(C=C)C=C)=[CH2:46].[Sn]>CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:26]([C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[C:3]=1[CH:45]=[CH2:46])=[CH2:27]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Similar to the synthesis of Example 203, a mixture of 1-(6-bromo-7-trifluoromethylsulfonyl-2-benzothiazolyl)-3-ethylurea (0.100 g, 0.22 mmol), lithium chloride (0.078 g, 1.84 mmol, 8.4 eq), triphenylphosphine (0.034 g, 0.13 mmol, 0.6 eq), Pd(PPh3)2Cl2 (0.018 g, 0.026 mmol, 0.12 eq), tetravinyltin (0.080 mL, 0.44 mmol, 2.0 eq), and a crystal of 2,6-di-tert-butyl-4-methylphenol was purged with nitrogen gas, and was heated at about 100° C. for about 18 hours. Additional tin reagent (0.080 mL, 0.44 mmol, 2.0 eq) was added to the mixture after the first 2 hours. The mixture was taken up in MeOH, filtered, and concentrated. Purification by HPLC and flash chromatography on SiO2 with ethyl acetate/methylene chloride (1/4) gave the desired compound 0.014 g (23%). LC/MS 274.3 (M+1); LC retention time 2.32 min.

Aufarbeitung

customSimilar to the synthesis of Example 203
customa crystal of 2,6-di-tert-butyl-4-methylphenol was purged with nitrogen gas
filtrationfiltered
concentrationconcentrated
customPurification by HPLC and flash chromatography on SiO2 with ethyl acetate/methylene chloride (1/4)

Quellen und Nachweise

ORD-Eintrag: ord-43344259a13143f2b751032583d652d5
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07091227B2

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