Water → HCID 82012920、化合物

HRID 1771804ノート

反応式

HRID 1771804 の反応式
[C:1]([C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]([F:14])[C:4]=1C(O)=O)#[N:2].CC[N:17](CC)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.O>C1COCC1>[NH2:17][C:4]1[C:8]([F:14])=[CH:9][CH:10]=[C:11]([O:12][CH3:13])[C:3]=1[C:1]#[N:2]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 834105191427408-14-7

生成物 1

HCID 82012920HCID 82012920、化合物収率 53%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 2-cyano-6-fluoro-3-methoxy-benzoic acid (2 g, 10.3 mmol, 1.0 eq) in THF (40 mL) were added Et3N (3.6 mL, 25.8 mmol, 2.5 eq) and DPPA (2.97 g, 10.8 mmol, 1.05 eq). The reaction was stirred at room temperature 3 h then water (10 mL) was added and the mixture was heated at reflux for 2 h. The THF was removed in vacuo and the aqueous solution diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 5:1) to give the title compound as an off-white solid (900 mg, 53%).

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 h
  3. customThe THF was removed in vacuo
  4. additionthe aqueous solution diluted with water
  5. extractionextracted with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue obtained
  11. customwas purified by column chromatography (petroleum ether:EtOAc, 5:1)

出典と根拠

ORDレコード
ord-2800b420d0a2492386183b8acda967cc
出典データセット
uspto-grants-2016_02
特許番号
US09249085B2

反応ノート

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