(+/-)-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 913847ノート

反応式

HRID 913847 の反応式
[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

参加物

3

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

(±)-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.

後処理

  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

出典と根拠

ORDレコード
ord-86111cab39144799b81bd882ccd0cb96
出典データセット
uspto-grants-2011_09
特許番号
US08026257B2

反応ノート

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