Cesium carbonate → (-)-2-(1-hydroxy-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)benzo[d]oxazole-5-carbonitrile

HRID 2174079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174079
C(OC([N:8]1[C:16]2[C:11](=[C:12]([C:20]([C:23]3[O:24][C:25]4[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][C:26]=4[N:27]=3)([OH:22])[CH3:21])[C:13]([O:18][CH3:19])=[CH:14][C:15]=2[CH3:17])[CH:10]=[CH:9]1)=O)(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+]>CO>[OH:22][C:20]([C:23]1[O:24][C:25]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][C:26]=2[N:27]=1)([C:12]1[C:13]([O:18][CH3:19])=[CH:14][C:15]([CH3:17])=[C:16]2[C:11]=1[CH:10]=[CH:9][NH:8]2)[CH3:21]

Komponenten

4

Edukt 2

HCID 10796Cesium carbonateHCID 86701712tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-hydroxyethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Produkt 1

HCID 86701713(-)-2-(1-hydroxy-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)benzo[d]oxazole-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A suspension of (±)-tert-butyl-4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-hydroxyethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (6.5 mg, 0.019 mmol) and Cs2CO3 (146 mg, 0.447 mmol) in MeOH (0.5 mL) was heated at 60° C. and stirred for 30 min. The reaction mixture was cooled to rt, quenched with a saturated aq. solution of ammonium chloride, diluted with AcOEt and water. The layers were separated and the aq. layer was extracted with AcOEt. The combined organic layers were dried over MgSO4, filtered and evaporated to dryness. The resulting residue was purified by flash chromatography (0-50% EtOAc:heptanes) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.88 (br. s., 1H) 8.36 (dd, J=1.39, 0.76 Hz, 1H) 7.65-8.00 (m, 2H) 7.28 (t, J=2.84 Hz, 1H) 6.95 (dd, J=3.03, 2.02 Hz, 1H) 6.62 (s, 1H) 6.31 (s, 1H) 3.19 (s, 3H) 2.44 (d, J=0.51 Hz, 3H) 1.95-2.02 (m, 3H). MS (ESI+) m/z 348.1 (M+H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to rt
  2. customquenched with a saturated aq. solution of ammonium chloride
  3. additiondiluted with AcOEt and water
  4. customThe layers were separated
  5. extractionthe aq. layer was extracted with AcOEt
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe resulting residue was purified by flash chromatography (0-50% EtOAc:heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-43f7eda0b18745dbb490a7a9d8337d93
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056874B2

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