Di-tert-butyl azodicarboxylate → HCID 89611118, 화합물

HRID 869064노트

반응식

HRID 869064 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 89611118HCID 89611118, 화합물수율 11.8%

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 887Methanol용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-df590c170538427a9f77e7e09472edef
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969341B2

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