Toluene → Prop-2-ynyl-(2,2,3,3-tetrafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-amine

HRID 1260342ノート

反応式

HRID 1260342 の反応式
[F:1][C:2]1([F:15])[O:7][C:6]2[CH:8]=[CH:9][C:10]([NH2:12])=[CH:11][C:5]=2[O:4][C:3]1([F:14])[F:13].[CH2:16](Br)[C:17]#[CH:18].C1(C)C=CC=CC=1>FC1C=CC=CC=1>[CH2:18]([NH:12][C:10]1[CH:9]=[CH:8][C:6]2[O:7][C:2]([F:1])([F:15])[C:3]([F:13])([F:14])[O:4][C:5]=2[CH:11]=1)[C:17]#[CH:16]

参加物

5

反応物 3

HCID 1140TolueneHCID 7842Propargyl bromideHCID 27765742,2,3,3-Tetrafluoro-1,4-benzodioxin-6-amine

生成物 1

HCID 86619165Prop-2-ynyl-(2,2,3,3-tetrafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-amine

試薬・触媒・溶媒 1

HCID 10008Fluorobenzene溶媒

反応条件

温度
50 °C

実験手順

2,2,3,3-Tetrafluoro-6-aminobenzodioxane (6.694 g, 30.0 mmol) and Aldrich basic alumina (activated, Brockmann 1, 150 mesh, CAS#1344-28-1) (51 g) were mixed in fluorobenzene (100 mL) and then treated with 80% propargyl bromide in toluene (2.56 mL, 23.0 mmol). The resulting mixture was thoroughly stirred and heated at 50° C. for 17 hours. The mixture was cooled to ambient temperature and filtered. The alumina was rinsed thoroughly with dichloromethane (150 mL), the filtrate was reduced in volume under reduced pressure, washed with concentrated aqueous NH4OH (5 mL), dried (Na2SO4), concentrated and chromatographed on silica eluting with 0-10% EtOAc/hexanes to provide the titled compound. 1H NMR (CDCl3) δ ppm 2.24 (t, 1H), 3.92 (m, 2H), 3.96 (m, 1H), 6.43 (d, 1H), 6.45 (dd, 1H), 6.96 (d, 1H); MS (DCI) 262 (M+H).

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. washThe alumina was rinsed thoroughly with dichloromethane (150 mL)
  4. washwashed with concentrated aqueous NH4OH (5 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customchromatographed on silica eluting with 0-10% EtOAc/hexanes

出典と根拠

ORDレコード
ord-a8b9a44aed464dd2a86176d50426552a
出典データセット
uspto-grants-2013_06
特許番号
US08470813B2

反応ノート

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