Phosphorus triiodide → HCID 86658386、化合物

HRID 455683ノート

反応式

HRID 455683 の反応式
IP(I)I.[Br:5][C:6]1[CH:7]=[C:8]2[C:18](=[CH:19][CH:20]=1)[O:17][C:11]1[CH:12]=[N:13][C:14]([Cl:16])=[CH:15][C:10]=1[C:9]2([CH2:22][O:23][CH:24]([CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[CH2:25][N+:26]([O-])=O)[NH2:21]>C(Cl)Cl>[NH2:21][C:9]1([CH2:22][O:23][CH:24]([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[C:25]#[N:26])[C:10]2[CH:15]=[C:14]([Cl:16])[N:13]=[CH:12][C:11]=2[O:17][C:18]2[C:8]1=[CH:7][C:6]([Br:5])=[CH:20][CH:19]=2

参加物

4

反応物 2

HCID 83485Phosphorus triiodideHCID 58465881HCID 58465881、化合物

生成物 1

HCID 86658386HCID 86658386、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

TEA (1.263 ml, 9.06 mmol) and triiodophosphine (1.243 g, 3.02 mmol) were added to 7-bromo-3-chloro-5-((1-cyclohexyl-2-nitroethoxy)methyl)-5H-chromeno[2,3-c]pyridin-5-amine (1.5 g, 3.02 mmol) in DCM (30.2 ml) at 0° C. The reaction was stirred 10 minutes before the ice water bath was removed and the reaction was allowed to come to RT. After 1.5 hours, the solution is cooled to 0° C. and quenched with saturated aqueous sodium bicarbonate, diluted with water, and extracted with DCM. The combined organic extracts were washed with 1N NaOH, water, saturated aqueous NaCl, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material. The crude material was purified by silica gel chromatography by eluting with 1:4 EtOAc in hexane, to provide 2-((5-amino-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)methoxy)-2-cyclohexylacetonitrile, [M+H]=462.0.

後処理

  1. customwas removed
  2. customto come to RT
  3. customquenched with saturated aqueous sodium bicarbonate
  4. additiondiluted with water
  5. extractionextracted with DCM
  6. washThe combined organic extracts were washed with 1N NaOH, water, saturated aqueous NaCl
  7. dry with materialdried over sodium sulfate
  8. filtrationThe solution was filtered
  9. concentrationconcentrated in vacuo
  10. customto give the crude material
  11. customThe crude material was purified by silica gel chromatography
  12. washby eluting with 1:4 EtOAc in hexane

出典と根拠

ORDレコード
ord-141ce87fdfa34f18b6d2bca8f9dac8f9
出典データセット
uspto-grants-2013_07
特許番号
US08497264B2

反応ノート

読み込み中…