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

HRID 1426081

反応式

HRID 1426081 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 206265543-(Benzyloxy)-5-bromopyridin-2-amine収率 27%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4f044eb2a0fc46f1b1e3b928467269a7
出典データセット
uspto-grants-2015_01
特許番号
US08933077B2

関連ノート

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