HCID 178451735、化合物 → Tert-butyl 5-(1-(tert-butoxycarbonyl)piperidin-4-yl)-3-iodo-1h-indazole-1-carboxylate

HRID 1520018ノート

反応式

HRID 1520018 の反応式
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[CH:9]=2)[NH:4][N:3]=1>C(#N)C>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][CH:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[N:3]=[C:2]3[I:1])[CH2:12][CH2:13]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

参加物

3

反応物 1

HCID 178451735HCID 178451735、化合物

生成物 1

HCID 67981049Tert-butyl 5-(1-(tert-butoxycarbonyl)piperidin-4-yl)-3-iodo-1h-indazole-1-carboxylate収率 148.7%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of tert-butyl 4-(3-iodo-1H-indazol-5-yl)piperidine-1-carboxylate (218. mg; 0.51 mmol; 1.0 eq.), di-tert-butyldicarboxylate (145 mg; 0.66 mmol; 1.3 eq.), diméthylamino-4-pyridine (12.5 mg; 0.10 mmol; 0.20 eq.) and TEA (86.0 μl; 0.61 mmol; 1.2 eq.) in acetonitrile (6.5 mL) was stirred at RT O/N. Acetonitrile was removed under reduced pressure, the residue was diluted with water and extracted three times with Ether. Combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude was purified by flash chromatography on silica (heptane/EtOAc, gradient from 90:10 to 75:25) to give the title compound as a colorless oil (200 mg, 74%). 1H NMR (300 MHz, DMSO-d6) δ 7.99 (d, J=8.7 Hz, 1H), 7.62 (dd, J=1.6, 8.7 Hz, 1H), 7.35 (s, 1H), 4.18-4.03 (m, 2H), 2.96-2.73 (m, 3H), 1.87-1.75 (m, 2H), 1.64 (s, 9H). 1.61-1.48 (m, 2H), 1.42 (s, 9H). (Condition A): Rt 6.33 min (purity 99.8%).

後処理

  1. customAcetonitrile was removed under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted three times with Ether
  4. washCombined organic phases were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was purified by flash chromatography on silica (heptane/EtOAc, gradient from 90:10 to 75:25)

出典と根拠

ORDレコード
ord-16a6b0ba1a0442c394c26ce5030eabf1
出典データセット
uspto-grants-2015_07
特許番号
US09073892B2

反応ノート

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