Ethyl orthoformate → tert-butyl 3-(6-bromo-1H-imidazo[4,5-c]pyridin-1-yl)piperidine-1-carboxylate

HRID 919645ノート

反応式

HRID 919645 の反応式
[NH2:1][C:2]1[C:3]([NH:9][CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)=[CH:4][C:5]([Br:8])=[N:6][CH:7]=1.[CH:23](OCC)(OCC)OCC>>[Br:8][C:5]1[N:6]=[CH:7][C:2]2[N:1]=[CH:23][N:9]([CH:10]3[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]3)[C:3]=2[CH:4]=1

参加物

3

反応物 2

HCID 31214Ethyl orthoformateHCID 86706485Tert-butyl 3-((5-amino-2-bromopyridin-4-yl)amino)piperidine-1-carboxylate

生成物 1

HCID 72344680tert-butyl 3-(6-bromo-1H-imidazo[4,5-c]pyridin-1-yl)piperidine-1-carboxylate収率 70%

実験手順

A mixture of tert-butyl 3-((5-amino-2-bromopyridin-4-yl)amino)piperidine-1-carboxylate (1.1 g, 3.0 mmol, 1.0 eq) in CH(OCH2CH3)3 (214 mg, 30 mmol, 10 eq) was refluxed for 40 h. Then the residual CH(OCH2CH3)3 was removed in vacuum and the crude product was purified by silica gel column chromatography with EtOAc in PE (½ v/v) to give the title compound (0.8 g, 70%) as yellow oil. 1H NMR (400 MHz, CDCl3) δ: 8.87 (s, 1H), 8.06 (s, 1H), 7.62 (s, 1H), 4.30-4.28 (m, 2H), 4.02-4.00 (m, 1H), 3.27-3.22 (m, 1H), 3.09-3.03 (m, 1H), 2.31-2.30 (m, 1H), 2.13-2.10 (m, 1H), 1.88-1.85 (m, 1H), 1.74-1.71 (m, 1H), 1.50 (s, 9H). ESI-MS (M+H+): 381.0.

後処理

  1. temperaturewas refluxed for 40 h
  2. customThen the residual CH(OCH2CH3)3 was removed in vacuum
  3. customthe crude product was purified by silica gel column chromatography with EtOAc in PE (½ v/v)

出典と根拠

ORDレコード
ord-1170db8207e944dd85bbd0dd9171b8a2
出典データセット
uspto-grants-2016_03
特許番号
US09273028B2

反応ノート

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