Reaktion #1773146

Reaktionsgleichung

acetic acid

3-trifluoromethylbenzoyl chloride

N,N-diisopropylethylamine

3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-(2-methyl-2-nitropropoxy)aniline

ammonium hydroxide

→

product

Ausbeute 90.0%

N-[4-(2-Amino-2-methyl-propoxy)-3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-phenyl]-3-trifluoromethyl-benzamide

Ausbeute 90.0%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 1M hydrochloric acid and saturated sodium bicarbonate
2. 2
   Trocknendried with sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Sonstigeevaporated to dryness
5. 5
   Extraktionthe product was extracted with ethyl acetate
6. 6
   WaschenThe ethyl acetate layer was washed with brine
7. 7
   Trocknendried with sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated to dryness
10. 10
    SonstigeThe crude product was purified by preparative LCMS

Vorschrift

A solution of 3-trifluoromethylbenzoyl chloride (17 μl, 0.11 mmol), N,N-diisopropylethylamine (21 μl, 0.12 mmol) and 3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-(2-methyl-2-nitropropoxy)aniline (37 mg, 0.10 mmol) in 0.5 mL of dichloromethane was stirred at room temperature. After 1 h the solution was diluted with dichloromethane, washed with 1M hydrochloric acid and saturated sodium bicarbonate, dried with sodium sulfate, filtered, and evaporated to dryness. The residue was taken up in methanol (0.4 mL), acetic acid (114 μl, 2.0 mmol) was added followed by zinc dust (65 mg, 1.0 mmol) and the mixture was stirred at room temperature. After 1 h the mixture was made strongly basic with conc. ammonium hydroxide, and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried with sodium sulfate, filtered, and evaporated to dryness. The crude product was purified by preparative LCMS and lyophilized to afford the product (46 mg, 74%) as a TFA-salt. LCMS m/z (%)=513.5 (M+H 81Br 71.7%), 511.3 (M+H 79Br 82.9%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.17 (s, 3 H), 1.18 (s, 3 H), 3.67 (s, 3 H), 3.84 (d, J=9.60 Hz, 1 H), 4.00 (d, J=9.85 Hz, 1 H), 7.31 (d, J=9.09 Hz, 1 H), 7.67 (s, 1 H), 7.70 (d, J=2.78 Hz, 1 H), 7.80 (t, J=7.71 Hz, 1 H), 7.86-7.94 (m, 3 H), 7.94-8.01 (m, 2 H), 8.26 (d, J=8.08 Hz, 1 H), 8.29 (s, 1 H), 10.57 (s, 1 H).

Quelle