Pyridine → HCID 57824451、化合物

HRID 1925430

反応式

HRID 1925430 の反応式
N1C=CC=CC=1.[F:7][C:8]([F:20])([F:19])[O:9][C:10]1[CH:18]=[CH:17][C:13]([CH:14]=[N:15][OH:16])=[CH:12][CH:11]=1.[NH2:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[CH2:27])=[CH:24][CH:23]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[F:7][C:8]([F:19])([F:20])[O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]2[CH2:27][CH:26]([C:25]3[CH:28]=[CH:29][C:22]([NH2:21])=[CH:23][CH:24]=3)[O:16][N:15]=2)=[CH:12][CH:11]=1

参加物

6

反応物 4

HCID 1049PyridineHCID 8471TriethylamineHCID 737004-AminostyreneHCID 2777199p-Trifluoromethoxybenzaldehyde oxime

生成物 1

HCID 57824451HCID 57824451、化合物収率 61.2%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒3 回

反応条件

温度
50 °C

実験手順

To a stirred solution of N-chlorosuccinimde (0.634 mmol, 85 μL) and pyridine (4 μL) in 2.5 mL of chloroform was added p-trifluoromethoxybenzaldehyde oxime (130 mg, 0.634 mmol). The reaction was heated at 50° C. for 3 h. 4-Aminostyrene (0.793 mmol, 93 μL) was then added followed by a solution of triethylamine (0.666 mmol, 93 μL) dissolved in 0.5 mL of CHCl3 dropwise. The reaction was stirred at 50° C. for 3 h. The cooled solution was diluted with chloroform (15 mL) and washed with water (2×10 mL). The organic phase was then dried over MgSO4, filtered and concentrated. The residue was purified via radial chromatography using a 2:1 hexane/EtOAc solution as the eluent (Rf=0.18) to afford 4-[3-(4-trifluoromethoxyphenyl)-4,5-dihydro-isoxazol-5-yl]-phenylamine (125 mg; 61%). 1H NMR (400 MHz, CDCl3) δ 7.73 (d, J=8.2 Hz, 2H), 7.25 (d, J=8.2 Hz, 2H), 7.17 (d, J=8.2 Hz, 2H), 6.68 (d, J=8.2 Hz, 2H), 5.65 (dd, J=10.9, 8.9 Hz, 1H), 3.55-3.75 (bs, 2H), 3.67 (dd, J=16.8, 10.9 Hz, 1H), 3.30 (dd, J=16.8, 8.9 Hz, 1H); EIMS 322 (M+).

後処理

  1. washwashed with water (2×10 mL)
  2. dry with materialThe organic phase was then dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified via radial chromatography

出典と根拠

ORDレコード
ord-14c5ce00a35c4752bbab5837cc7a559b
出典データセット
uspto-grants-2012_05
特許番号
US08178658B2

関連ノート

読み込み中…