Toluene → methyl 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-ethylbenzoate

HRID 915586

Reaktionsgleichung

Reaktionsgleichung von HRID 915586
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]2[N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[N:16]=[C:15]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:14]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:29](B(O)O)[CH3:30].C(Cl)Cl.C1(C)C=CC=CC=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[C:25]([C:15]1[CH:14]=[C:13]([NH:12][C:5]2[CH:4]=[CH:3][C:2]([CH2:29][CH3:30])=[CH:11][C:6]=2[C:7]([O:9][CH3:10])=[O:8])[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[N:16]=1)([CH3:28])([CH3:27])[CH3:26]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 6344DichloromethaneHCID 521157Ethylboronic acidHCID 58958623methyl 5-bromo-2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}benzoate

Produkt 1

HCID 58958598methyl 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-ethylbenzoateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a mixture of methyl 5-bromo-2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}benzoate (Example 234, 1.15 g, 4.13 mmol), ethylboronic acid (1.16 g, 15.7 mmol), and Pd(dppf)Cl2.CH2Cl2 (114 mg, 0.16 mmol) was added toluene (20 mL) and dioxane (5 mL). The resulting solution was degassed under nitrogen for 30 min, followed by addition of sodium bicarbonate (2 M aq solution, 15 mL). The mixture was then heated to 85° C. for 16 h. The reaction mixture was allowed to cool to rt. The solvent was removed under reduced pressure, and the residue was purified by silica gel flash chromatography using 0 to 10% ethyl acetate in hexanes to afford 606 mg (61%) of the title compound. 1H NMR (300 MHz, CD2Cl2) δ 9.17 (s, 1H), 7.68 (s, 1H), 7.22-7.33 (m, 6H), 6.08 (s, 1H), 3.70 (s, 3H), 2.51 (q, 2H), 2.05 (s, 3H), 1.30 (s, 9H), 1.14 (t, 3H). ES-MS m/z 392.2 (MH+); HPLC RT (min) 4.62.

Aufarbeitung

  1. customThe resulting solution was degassed under nitrogen for 30 min
  2. additionfollowed by addition of sodium bicarbonate (2 M aq solution, 15 mL)
  3. temperatureto cool to rt
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c32987e78db14c6d91d9166ea5590b2e
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265144B2

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