Pyridine → HCID 56982471、化合物

HRID 369740ノート

反応式

HRID 369740 の反応式
[NH2:1][C:2]1[C:7]([C:8]([OH:20])([C:13]#[C:14][C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[C:9]([F:12])([F:11])[F:10])=[CH:6][C:5]([Cl:21])=[CH:4][CH:3]=1.N1C=CC=CC=1.Br[CH2:29][CH2:30][C:31](Br)=[O:32]>CCOCC>[Cl:21][C:5]1[CH:4]=[CH:3][C:2]2[NH:1][C:31](=[O:32])[C@H:30]([CH3:29])[O:20][C@:8]([C:13]#[C:14][C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)([C:9]([F:10])([F:11])[F:12])[C:7]=2[CH:6]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 10998423BromopropionylbromideHCID 54107311HCID 54107311、化合物

生成物 1

HCID 56982471HCID 56982471、化合物

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

To a stirred ice-cooled solution of 265 mg of 6-amino-3-chloro-α-(furan-2-yl)ethynyl-α-(trifluoromethyl)benzyl alcohol in 10 mL of dry ether was added 0.150 mL of dry pyridine and 0.100 mL of bromopropionyl bromide. After 30 min, the reaction mixture was diluted with ether, washed with water and aqueous sodium bicarbonate, dried and evaporated. The residue was dissolved in 10 mL of dry DMF at 0°, 25 mg of 100% sodium hydride was added, and the resulting mixture was stirred for 15 min at 0° and at room temperature for 30 min. The reaction mixture was then poured onto water and extracted twice with ether. The combined extracts were washed with water and brine, dried and evaporated to a residue which was purified by column chromatography on silica gel (elution with 17-33% ethyl acetate in hexanes) affording after crystallization from ethyl acetale/hexanes 5 mg of the title compound: HRMS: Calcd. for C17H12NO3ClF3 (M+H)+ : 369.037956. Found: 369.036835.

後処理

  1. washwashed with water and aqueous sodium bicarbonate
  2. customdried
  3. customevaporated
  4. dissolutionThe residue was dissolved in 10 mL of dry DMF at 0°
  5. addition25 mg of 100% sodium hydride was added
  6. additionThe reaction mixture was then poured onto water
  7. extractionextracted twice with ether
  8. washThe combined extracts were washed with water and brine
  9. customdried
  10. customevaporated to a residue which
  11. customwas purified by column chromatography on silica gel (elution with 17-33% ethyl acetate in hexanes)
  12. customaffording
  13. customafter crystallization from ethyl acetale/hexanes 5 mg of the title compound

出典と根拠

ORDレコード
ord-c15cf1e3c77c47bf924709cbe1c13110
出典データセット
uspto-grants-2000_10
特許番号
US06140320

反応ノート

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