Triethylamine → N-(4-(4-oxo-7-((trimethylsilyl)ethynyl)-4H-chromen-3-yl)phenyl)methanesulfonamide

HRID 1188260ノート

反応式

HRID 1188260 の反応式
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:28])[C:12]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=3)=[CH:13][O:14]2)=[CH:9][CH:8]=1)(=O)=O.[CH3:31][Si:32]([C:35]#[CH:36])([CH3:34])[CH3:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[O:28]=[C:11]1[C:10]2[C:15](=[CH:16][C:7]([C:36]#[C:35][Si:32]([CH3:34])([CH3:33])[CH3:31])=[CH:8][CH:9]=2)[O:14][CH:13]=[C:12]1[C:17]1[CH:18]=[CH:19][C:20]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])=[CH:21][CH:22]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 866950543-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate

生成物 1

HCID 86695055N-(4-(4-oxo-7-((trimethylsilyl)ethynyl)-4H-chromen-3-yl)phenyl)methanesulfonamide

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
85 °C

実験手順

3-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate (2.5 g, 5.39 mmol), trimethylsilylacetylene (0.92 ml, 1.2 eq), PdCl2(PPh3)2 (175 mg, 0.05 eq), copper iodide (28.8 mg 0.03 eq), triphenylphosphine (40 mg 0.03 eq) and triethylamine (3.12 ml, 4.0 eq) were combined in dry tetrahydrofuran (10 ml) and heated in microwave for 30 minutes at 85° C. The reaction mixture was partitioned between ethyl acetate and water, the organic phase dried with magnesium sulfate, and solvent removed under reduced pressure. The crude product was heated in acetonitrile, cooled down and the solids were filtered off. This procedure was repeated twice in order to afford N-(4-(4-oxo-7-((trimethylsilyl)ethynyl)-4H-chromen-3-yl)phenyl)methanesulfonamide.

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialthe organic phase dried with magnesium sulfate, and solvent
  3. customremoved under reduced pressure
  4. temperatureThe crude product was heated in acetonitrile
  5. temperaturecooled down
  6. filtrationthe solids were filtered off

出典と根拠

ORDレコード
ord-887945504d6445d8a911b2dba30c79c0
出典データセット
uspto-grants-2014_03
特許番号
US08673966B2

反応ノート

読み込み中…