N-bromobutanimide → 3-(Benzyloxy)-5-bromopyridin-2-amine

HRID 1426081

반응식

HRID 1426081 반응식
[CH2:1]([O:8][C:9]1[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O>C(#N)C>[CH2:1]([O:8][C:9]1[C:10]([NH2:15])=[N:11][CH:12]=[C:13]([Br:16])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 903342-Amino-3-benzyloxypyridine

생성물 1

HCID 206265543-(Benzyloxy)-5-bromopyridin-2-amine수율 27%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
0 °C

실험 절차

3-(Benzyloxy)pyridin-2-amine (25.0 g, 124.9 mmol) was added to acetonitrile (300 mL) and cooled to 0° C. 1-Bromopyrrolidine-2,5-dione (22.22 g, 124.9 mmol) was added portionwise and the reaction mixture was stirred for 15 minutes, then concentrated to dryness. The residue was dissolved in EtOAc and partitioned with water. The organic layer was washed twice with saturated sodium bicarbonate and once with brine. Activated charcoal was added to the organic layer, and the organic layer was warmed to reflux, then cooled, filtered through a plug of celite, and concentrated to give 9.4 g of the title compound. The celite and charcoal were resuspended in EtOAc and filtered through a celite plug to give an additional 3.6 g of the title compound, to provide a total of 12.0 g (34.3% yield). 1H NMR (CDCl3) δ 7.74 (d, 1H), 7.41 (m, 5H), 7.08 (d, 1H), 5.04 (s, 2H), 4.74 (bs, 2H). Mass spectrum (apci) m/z=279.1 (M+H).

후처리

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in EtOAc
  3. custompartitioned with water
  4. washThe organic layer was washed twice with saturated sodium bicarbonate and once with brine
  5. additionActivated charcoal was added to the organic layer
  6. temperaturethe organic layer was warmed
  7. temperatureto reflux
  8. temperaturecooled
  9. filtrationfiltered through a plug of celite
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4f044eb2a0fc46f1b1e3b928467269a7
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933077B2

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