Di-tert-butyl azodicarboxylate → HCID 89611118、化合物

HRID 869064ノート

反応式

HRID 869064 の反応式
[Br:1][C:2]1[CH:7]=[C:6](B(O)O)[C:5]([O:11][CH3:12])=[CH:4][N:3]=1.[N:13]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[N:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>CO.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:28][C:25]([O:24][C:22]([N:13]([C:6]1[C:5]([O:11][CH3:12])=[CH:4][N:3]=[C:2]([Br:1])[CH:7]=1)[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:23])([CH3:26])[CH3:27]

参加物

5

反応物 2

HCID 97268Di-tert-butyl azodicarboxylateHCID 44119383(2-Bromo-5-methoxypyridin-4-yl)boronic acid

生成物 1

HCID 89611118HCID 89611118、化合物収率 11.8%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

A mixture of 2-bromo-5-methoxypyridine-4-boronic acid (10 g, 43.1 mmol), di-tert-butyl azodicarboxylate (9.93 g, 43.1 mmol), and copper(II) acetate (7.48 mg, 0.041 mmol) in MeOH (150 mL) was stirred 20 h at 50° C., filtered, concentrated, diluted with brine (100 mL), and extracted with EtOAc. The organic layers were combined, washed with brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel column chromatography (hexane/EtOAc, 95:5→3:1) to provide 2.13 g of the title compound. tR: 1.21 min (LC-MS 4); ESI-MS: 418.2 [M+H]+ (LC-MS 4); Rf=0.67 (hexane/EtOAc, 1:1).

後処理

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additiondiluted with brine (100 mL)
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (hexane/EtOAc, 95:5→3:1)

出典と根拠

ORDレコード
ord-df590c170538427a9f77e7e09472edef
出典データセット
uspto-grants-2015_03
特許番号
US08969341B2

反応ノート

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