Diethylamine → Methyl 3-amino-4-(2,6-dimethylphenylethynyl)-benzoate

HRID 1514929

反応式

HRID 1514929 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1I)[C:5]([O:7][CH3:8])=[O:6].[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[C:21]#[CH:22].C(NCC)C.C(OCC)(=O)C>CN(C=O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:22]#[C:21][C:15]1[C:16]([CH3:20])=[CH:17][CH:18]=[CH:19][C:14]=1[CH3:13])[C:5]([O:7][CH3:8])=[O:6]

参加物

8

反応物 4

HCID 8021DiethylamineHCID 8857Ethyl AcetateHCID 130076692-Ethynyl-1,3-dimethylbenzeneHCID 21628210Methyl 3-amino-4-iodobenzoate

生成物 1

HCID 66965741Methyl 3-amino-4-(2,6-dimethylphenylethynyl)-benzoate

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of methyl 3-amino-4-iodobenzoate (920 mg, 3.32 mmol), 2,6-dimethylphenylacetylene (540 mg, 4.15 mmol),), bis-(triphenylphosphine) palladium (II) chloride (47 mg, 67 μmol), diethylamine (486 mg, 66 mmol), and copper (I) iodide (19 mg, 100 μmol) in DMF (10 mL) was heated at 120° C. in a microwave apparatus for 10 min. The mixture was poured into ethyl acetate and extracted six times with brine. The organic phase was dried, filtered, and the solvent was removed under reduced pressure to leave a residue that was chromatographed using a gradient of 0-30% heptane/ethyl acetate to afford methyl 3-amino-4-(2,6-dimethylphenylethynyl)-benzoate.

後処理

  1. extractionextracted six times with brine
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customto leave a residue that
  6. customwas chromatographed

出典と根拠

ORDレコード
ord-1f95b15787b8488a885bd3de7e50aa83
出典データセット
uspto-grants-2012_07
特許番号
US08222248B2

関連ノート

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