Benzoyl Peroxide → tert-Butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

HRID 343120ノート

反応式

HRID 343120 の反応式
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:3]=1.[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:3]=1

参加物

5

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 57370583Tert-butyl 3-methyl-1H-pyrazolo[3,4-B]pyridine-1-carboxylate

生成物 1

HCID 10828872tert-Butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate収率 52.9%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A stirring solution of 240 mg (1.03 mmol) of 3-Methyl-1 tert-butoxycarbonyl-pyrazolo[3,4-b]pyridine, prepared as in Part B, in 10 mL of CCl4 is heated to reflux, and then a mixture of 220 mg (1.23 mmol, 1.2 equiv) of N-bromosuccinimide and 25 mg (0.10 mmol, 0.1 equiv) of benzoyl peroxide is added all at once as a solid. The resulting solution is heated at reflux for 3.5 h, then cooled to RT. The reaction mixture is filtered through a pad of Celite to remove the precipitated succinimide, and the solvent is removed in vacuo. Purification of the crude material by silica gel flash column chromatography using hexane/EtOAc 3/1 as eluent afforded 170 mg of the title compound as a white solid: 1H NMR (CDCl3, 400 MHz) δ8.75 (dd, 1H, J=1.4, 4.6), 8.21 (dd, 1H, J=1.4, 8.0), 7.32 (dd, 1H, J=4.6, 8.0), 4.74 (s, 2H), 1.70 (s, 9H).

後処理

  1. temperatureto reflux
  2. additionis added all at once as a solid
  3. temperatureThe resulting solution is heated
  4. temperatureat reflux for 3.5 h
  5. filtrationThe reaction mixture is filtered through a pad of Celite
  6. customto remove the precipitated succinimide
  7. customthe solvent is removed in vacuo
  8. customPurification of the crude material by silica gel flash column chromatography

出典と根拠

ORDレコード
ord-e9db1058ccff47018fcce5de052021c6
出典データセット
uspto-grants-1999_01
特許番号
US05859007

反応ノート

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