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Methyl iodide → 1-(4-Fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-morpholin-4-ylpyrimidin-2-yl)propan-1-one

HRID 2278585
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2278585
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[C:11](=[O:27])[CH2:12][C:13]1[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:14]=1.[CH3:28][Si]([N-][Si](C)(C)C)(C)C.[K+].CI>O1CCCC1.[Cl-].[NH4+].C(OCC)(=O)C>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[C:11](=[O:27])[CH:12]([C:13]1[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:14]=1)[CH3:28]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 6328Methyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 682817151-(4-Fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-morpholin-4-ylpyrimidin-2-yl)ethanone

Produkt 1

HCID 682815811-(4-Fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-morpholin-4-ylpyrimidin-2-yl)propan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×
HCID 8857Ethyl AcetateLösungsmittel
HCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

300 mg of 1-(4-fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-morpholin-4-yl-pyrimidin-2-yl)ethanone dissolved in 10 ml of tetrahydrofuran are cooled to −78° C. using a dry ice bath. 2.65 ml of 1N potassium bis(trimethylsilyl)amide in THF are slowly added while maintaining the temperature at −75° C. After 30 minutes of stirring, 0.125 ml of methyl iodide is added and the stirring is continued for 2 h 15. The reaction mixture is diluted with 50 ml of a saturated ammonium chloride solution and 30 ml of ethyl acetate. After settling out, the organic phase is washed with 5 times 15 ml of water, dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue is purified by silica column chromatography, elution being carried out with a 99/01 mixture of dichloromethane and methanol, so as to give 215 mg of 1-(4-fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-morpholin-4-ylpyrimidin-2-yl)propan-1-one in the form of a white solid, the characteristics of which are the following:

Aufarbeitung

  1. temperaturewhile maintaining the temperature at −75° C
  2. waitthe stirring is continued for 2 h
  3. washthe organic phase is washed with 5 times 15 ml of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica column chromatography, elution
  8. additionbeing carried out with a 99/01 mixture of dichloromethane and methanol

Quellen und Nachweise

ORD-Eintrag
ord-0dce945062ce47eba153b0a9ca18cfdb
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09133168B2

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