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

HRID 1514929

반응식

HRID 1514929 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1f95b15787b8488a885bd3de7e50aa83
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222248B2

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