Dimethylformamide → HCID 69670779、化合物

HRID 2400287ノート

反応式

HRID 2400287 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 69670779HCID 69670779、化合物収率 92.6%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
160 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-891e5a9a46d84c68bce523da5c1f53f8
出典データセット
uspto-grants-2014_08
特許番号
US08796247B2

反応ノート

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