Triphenylphosphine → 2-[1-(2-fluorobenzenesulfonyl)-1H-indol-4-yloxy]ethyl methylcarbamic acid tert-butyl ester

HRID 1835916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1835916
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27]([N:30]1[C:38]2[C:33](=[C:34]([OH:39])[CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31]1)(=[O:29])=[O:28].[C:40]([O:44][C:45](=[O:51])[N:46]([CH2:48][CH2:49]O)[CH3:47])([CH3:43])([CH3:42])[CH3:41].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:40]([O:44][C:45](=[O:51])[N:46]([CH2:48][CH2:49][O:39][C:34]1[CH:35]=[CH:36][CH:37]=[C:38]2[C:33]=1[CH:32]=[CH:31][N:30]2[S:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[F:20])(=[O:28])=[O:29])[CH3:47])([CH3:43])([CH3:42])[CH3:41]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanolHCID 5462977Diethyl azodicarboxylateHCID 114718421-(2-fluorobenzenesulfonyl)-4-hydroxy-1H-indole

Produkt 1

HCID 111783912-[1-(2-fluorobenzenesulfonyl)-1H-indol-4-yloxy]ethyl methylcarbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 100 mL flask equipped with a magnetic stirrer and a rubber septum was charged with triphenyl phosphine (0.506 g, 0.0019 mol) and 1-(2-fluorobenzenesulfonyl)-4-hydroxy-1H-indole (0.330 g, 0.0012 mol), and purged with N2. The mixture was cooled to 0° C. and freshly distilled THF was added (45 mL). A solution of 2-hydroxyethyl methylcarbamic acid tert-butyl ester (0.317 g, 0.0018 mol) and diethylazodicarboxylate (0.337 g, 0.0019 mol) in 5 mL of THF was added dropwise at 0° C. to give a yellow solution. The reaction mixture was warmed to ambient temperature and stirred for 72 hours, concentrated in vacuo and the resulting crude oil was purified by flash chromatography using a 25:75 of hexanes/ethyl acetate mixture to give 2-[1-(2-fluorobenzenesulfonyl)-1H-indol-4-yloxy]ethyl methylcarbamic acid tert-butyl ester as a clear oil (0.483 mg; 89%). 1H NMR (300 MHz, CDCl3) δ: 1.44 (bs, 9 H), 3.01 (s, 3 H), 3.65 (bs, 2 H), 4.19 (bs, 2 H), 6.65 (d, 1 H, J=8.03), 6.76 (d, 1 H, J=3.77), 7.09 (t, 1 H, J=8.67). 7.17 (t, 1 H, J=8.11), 7.28 (t, 1 H, J=7.73), 7.44 (d, 1 H, J=8.29), 7.55 (m, 2 H), 803 (t, 1 H, J=7.44).

Aufarbeitung

  1. customA 100 mL flask equipped with a magnetic stirrer
  2. custompurged with N2
  3. additionfreshly distilled THF was added (45 mL)
  4. customto give a yellow solution
  5. temperatureThe reaction mixture was warmed to ambient temperature
  6. concentrationconcentrated in vacuo
  7. customthe resulting crude oil was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ac54dedbbf3447e681d9558605407024
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06774241B2

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