(+/-)-tert-Butyl 4-((1-(5-bromo-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)ethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate → (+/-)-5-Bromo-7-(1-((4-(4-fluorophenyl)piperidin-4-yl)methoxy)ethyl)-1H-indazole

HRID 913847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 913847
[Br:1][C:2]1[CH:10]=[C:9]([CH:11]([O:13][CH2:14][C:15]2([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)[CH3:12])[C:8]2[C:4](=[CH:5][N:6](COCC[Si](C)(C)C)[N:7]=2)[CH:3]=1>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]([O:13][CH2:14][C:15]3([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[CH3:12])[CH:10]=1)[NH:7][N:6]=[CH:5]2

Komponenten

3

Edukt 1

HCID 57546111(+/-)-tert-Butyl 4-((1-(5-bromo-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)ethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate

Produkt 1

HCID 57546134(+/-)-5-Bromo-7-(1-((4-(4-fluorophenyl)piperidin-4-yl)methoxy)ethyl)-1H-indazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

(±)-tert-Butyl 4-((1-(5-bromo-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)ethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate (40 mg, 0.075 mmol) was dissolved in trifluoroacetic acid (20% in dichloromethane, 1.25 mL) and stirred at room temperature for 30 min. The reaction was concentrated and loaded onto a strong cation exchange cartridge in methanol. The cartridge was flushed with several volumes of methanol which were discarded. The product was eluted with 2M ammonia in methanol and concentrated. 1H-NMR (CDCl3, 500 MHz) δ 10.05 (bs, 1H), 7.90 (s, 1H), 7.73 (d, J=1.5, 1H), 7.25 (m, 2H), 7.10 (d, J=1.5, 1H), 7.05 (m, 2H), 4.48 (q, J=6.4, 1H), 3.39 (d, J=8.9, 1H), 3.25 (d, J=8.9, 1H), 2.91 (m, 1H), 2.84 (m, 1H), 2.75 (m, 1H), 2.68 (m, 1H), 1.60-2.30 (bs, 1H), 2.20 (m, 1H), 2.04 (m, 1H), 1.89 (m, 1H), 1.80 (m, 1H), 1.42 (d, J=6.7, 3H); 13C NMR (126 MHz, CDCl3) δ ppm 162.5, 160.6, 139.5, 135.9, 133.7, 128.7 (d, J=7.7), 128.0, 126.5, 125.5, 122.3, 115.6, 115.4, 113.5, 79.0, 78.2, 50.7, 42.6, 42.5, 41.4, 33.9, 33.6, 22.2.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. customThe cartridge was flushed with several volumes of methanol which
  3. washThe product was eluted with 2M ammonia in methanol
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-86111cab39144799b81bd882ccd0cb96
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026257B2

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