Potassium Carbonate → methyl {3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-cyclopropylpyridin-3-yl]-4-methoxyphenyl}acetate

HRID 604673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604673
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[C:28]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH:29]=[CH:30][C:31]=4[O:32][CH3:33])=[CH:24][CH:23]=[C:22](Cl)[N:21]=3)[C@H:14]2[CH3:40])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH:43]1(B(O)O)[CH2:45][CH2:44]1.C([O-])([O-])=O.[K+].[K+]>[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2].C1COCC1>[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[C:28]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH:29]=[CH:30][C:31]=4[O:32][CH3:33])=[CH:24][CH:23]=[C:22]([CH:43]4[CH2:45][CH2:44]4)[N:21]=3)[C@H:14]2[CH3:40])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 57576209methyl {3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-chloropyridin-3-yl]-4-methoxyphenyl}acetate

Produkt 1

HCID 57576297methyl {3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-cyclopropylpyridin-3-yl]-4-methoxyphenyl}acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178454861HCID 178454861, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A flask was charged with methyl {3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-chloropyridin-3-yl]-4-methoxyphenyl}acetate (42 mg, 0.0681 mmol), cyclopropyl boronic acid (58.5 mg, 0.681 mmol), 1,1′-bis(di-t-butylphosphino)ferrocene palladium dichloride (8.9 mg, 0.014 mmol), THF (1 mL), and 1M K2CO3 (1 mL, 1 mmol). The reaction was degassed with N2, and heated to 60° C. for 8 hours. The reaction was then cooled to room temperature, diluted with EtOAc (35 mL) and washed with water and brine (10 mL each). The organic layer was dried (Na2SO4), filtered, and concentrated. Purification of the residue by flash chromatography (0 to 70% EtOAc/hexanes) afforded methyl {3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-cyclopropylpyridin-3-yl]-4-methoxyphenyl}acetate. LCMS=623-4 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 6.90-7.84 (m, 8H), 4.82-5.66 (m, 2H), 3.57-4.13 (m, 10H), 2.06 (m, 1H), 1.00-1.06 (m, 4H), 0.62 (bs, 3H).

Aufarbeitung

  1. customThe reaction was degassed with N2
  2. temperatureThe reaction was then cooled to room temperature
  3. additiondiluted with EtOAc (35 mL)
  4. washwashed with water and brine (10 mL each)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by flash chromatography (0 to 70% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-969088c3a43b46738cb17434ae528601
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910592B2

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