Potassium Carbonate → Diethyl 2-(3-ethynylphenylamino)ethylphosphonate

HRID 1782175노트

반응식

HRID 1782175 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])#[CH:2].Br[CH2:11][CH2:12][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:3]1[CH:4]=[C:5]([NH:6][CH2:11][CH2:12][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])[CH:7]=[CH:8][CH:9]=1)#[CH:2]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 79218Diethyl (2-bromoethyl)phosphonateHCID 104682Benzenamine, 3-ethynyl-

생성물 1

HCID 57588428Diethyl 2-(3-ethynylphenylamino)ethylphosphonate수율 7.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

3-Ethynyl aniline (2.36 g, 22.1 mmol), diethyl 2-bromoethylphosphonate (5.41 g, 22.1 mmol) and potassium carbonate (3.1 gm, 22.1 mmol) were heated at 90° C. in anhydrous acetonitrile (40 mL) for 26 h. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel, eluting with 1:1 ethyl acetate:hexanes followed by 97:3 methylene chloride:methanol to provide diethyl 2-(3-ethynylphenylamino)ethylphosphonate (450 mg) as a yellow oil. 1H NMR (CDCl3) δ 7.15 (t, 1H), 6.83 (d, 1H), 6.70 (br s, 1H), 6.60 (m, 1H), 4.10 (m, 4H), 3.41 (m, 2H), 3.00 (s, 1H), 2.10 (m, 2H), 1.35 ppm (m, 6H). MW=281 confirmed by LC-MS, tr=11.65 min (Method Y) MH+=282.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by flash column chromatography on silica gel
  9. washeluting with 1:1 ethyl acetate

출처 및 근거

ORD 기록
ord-8afee5cf262241de8d877b4321071517
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07498353B2

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