Diisopropylethylamine → HCID 44481474, 화합물

HRID 452788

반응식

HRID 452788 반응식
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]3[CH:18]=[C:19]([C:22]4[O:23][C:24]([CH3:27])=[N:25][N:26]=4)[CH:20]=[CH:21][C:16]=3[O:15][CH:14]=2)=[CH:9][CH:8]=1)(=O)=O.[P:30]([O-:35])([O:33][CH3:34])[O:31][CH3:32].C(N(CC)C(C)C)(C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:32][O:31][P:30]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]3[CH:18]=[C:19]([C:22]4[O:23][C:24]([CH3:27])=[N:25][N:26]=4)[CH:20]=[CH:21][C:16]=3[O:15][CH:14]=2)=[CH:9][CH:8]=1)(=[O:35])[O:33][CH3:34]

참가 물질

7

반응물 3

HCID 81531DiisopropylethylamineHCID 21884954DimethylphosphiteHCID 866400464-[5-(5-Methyl-1,3,4-oxadiazol-2-yl)-1-benzofuran-3-yl]phenyl trifluoromethanesulfonate

생성물 1

HCID 44481474HCID 44481474, 화합물수율 55%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1-benzofuran-3-yl]phenyl trifluoromethanesulfonate (391 mg, 0.900 mmol), dimethyl phosphite (0.165 mL, 1.80 mmol), tetrakis(triphenylphosphine)palladium(0) (104 mg, 0.0900 mmol) and N,N-diisopropylethylamine (0.314 mL, 1.80 mmol) in toluene (5 mL) was stirred at 100° C. for 2 hr under an argon atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate, washed with 1M hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate) and recrystallized from hexane/ethyl acetate to give the title compound (190 mg, yield 55%) as colorless crystals.

후처리

  1. temperatureAfter cooling
  2. washwashed with 1M hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (ethyl acetate)
  6. customrecrystallized from hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-c4cbe7b36a8346898501a35437bcc19e
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492378B2

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