Isopropylamine → Methyl 4-(5-chloro-2-(isopropylamino)pyridin-4-yl)benzoate

HRID 968693ノート

反応式

HRID 968693 の反応式
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15]([Cl:16])=[CH:14][N:13]=[C:12](F)[CH:11]=2)=[CH:6][CH:5]=1.[CH:19]([NH2:22])([CH3:21])[CH3:20]>CS(C)=O.O>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15]([Cl:16])=[CH:14][N:13]=[C:12]([NH:22][CH:19]([CH3:21])[CH3:20])[CH:11]=2)=[CH:6][CH:5]=1

参加物

5

反応物 2

HCID 6363IsopropylamineHCID 694221754-(5-Chloro-2-fluoropyridin-4-yl)-benzoic acid methyl ester

生成物 1

HCID 69423277Methyl 4-(5-chloro-2-(isopropylamino)pyridin-4-yl)benzoate収率 67%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

4-(5-Chloro-2-fluoropyridin-4-yl)-benzoic acid methyl ester (90 mg, 0.34 mmol) was dissolved in DMSO in a screw cap tube and 0.5 mL isopropylamine was added. The tube was sealed and heated to 90° C. for 2 days. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to an oil, which was purified by chromatography on silica (EtOAc 0 to 20%/hexanes) to give 70 mg of 4-(5-chloro-2-isopropylamino-pyridin-4-yl)-benzoic acid methyl ester, 0.23 mmol, 67% yield. 1H NMR 500 MHz (CDCl3): 8.08 (m, 3H), 7.45 (d, 2H), 6.22 (s, 1H), 4.37 (d, 1H), 3.88 (s, 3H), 3.80 (m, 1H), 1.17 (d, 6H).

後処理

  1. customcap tube
  2. customThe tube was sealed
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to an oil, which
  7. customwas purified by chromatography on silica (EtOAc 0 to 20%/hexanes)

出典と根拠

ORDレコード
ord-7cedb68176ad4c92a53bbfcd82b2ee5a
出典データセット
uspto-grants-2007_12
特許番号
US07304071B2

反応ノート

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