Dimethylformamide → HCID 69670779, 화합물

HRID 2400287노트

반응식

HRID 2400287 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[CH2:11][CH:12](O)[CH:13]([CH3:16])[CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+].BrC1C(C)=CC(C)=CC=1C.CN(C)C=O>[Pd].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.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.O.C(OCC)(=O)C>[CH3:16][CH:13]([C:12]1[NH:1][C:2]2[C:3]([CH:11]=1)=[CH:4][C:5]([O:9][CH3:10])=[C:6]([Cl:8])[CH:7]=2)[CH2:14][CH3:15]

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 684732-BromomesityleneHCID 696710981-(2-Amino-4-chloro-5-methoxyphenyl)-3-methylpentan-2-ol

생성물 1

HCID 69670779HCID 69670779, 화합물수율 92.6%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
160 °C

실험 절차

A mixture of 1-(2-amino-4-chloro-5-methoxyphenyl)-3-methylpentan-2-ol (602 mg), tetrakis(triphenylphosphine) palladium(0) (135 mg), potassium carbonate (646 mg), 2-bromomesitylene (0.420 mL), and N,N-dimethylformamide (11.7 mL) was stirred at 160° C. for 1 hour under microwave irradiation. To the reaction mixture were added ethyl acetate and water to separate the organic layer. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (514 mg). 1H-NMR (CDCl3) δ ppm: 0.91 (3H, t, J=7.4 Hz), 1.32 (3H, d, J=6.8 Hz), 1.55-1.80 (2H, m), 2.70-2.90 (1H, m), 3.91 (3H, s), 6.10-6.20 (1H, m), 7.05 (1H, s), 7.25-7.35 (1H, m), 7.50-8.00 (1H, br).

후처리

  1. customto separate the organic layer
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-891e5a9a46d84c68bce523da5c1f53f8
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08796247B2

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