Diisopropylethylamine → HCID 44481474、化合物

HRID 452788

反応式

HRID 452788 の反応式
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]

参加物

7

反応物 3

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

生成物 1

HCID 44481474HCID 44481474、化合物収率 55%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c4cbe7b36a8346898501a35437bcc19e
出典データセット
uspto-grants-2013_07
特許番号
US08492378B2

関連ノート

読み込み中…