4-Chloroaniline → HCID 50943107、化合物

HRID 1920083ノート

反応式

HRID 1920083 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH:11](O)[C:12]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)=[O:13])=[O:9])=[N:6][CH:7]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[Cl:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1>C(Cl)(Cl)Cl.C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH:11]([NH:36][C:35]2[CH:37]=[CH:38][C:32]([Cl:31])=[CH:33][CH:34]=2)[C:12]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)=[O:13])=[O:9])=[N:6][CH:7]=1

参加物

6

反応物 3

HCID 78124-ChloroanilineHCID 24819Phosphorus pentachlorideHCID 58149557HCID 58149557、化合物

生成物 1

HCID 50943107HCID 50943107、化合物収率 37%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

5-bromo-N-(1-hydroxy-2-(naphthalen-1-yl)-2-oxoethyl)picolinamide 113 (0.74 g, 1.93 mmol) in chloroform (20 mL) was reacted with PCl5 (0.43 g, 1.96 mmol). The mixture was heated to 50° C. for 30 minutes and cooled to 0° C. 4-Chloroaniline 114 (0.512 g, 4.01 mmol) in THF (10 mL) was added and allowed to react for 1 hour. The reaction was quenched with water and the product was extracted with ethyl acetate. The organic solution was dried over MgSO4, filtered and concentrated onto silica gel. The product was purified by auto flash column chromatography (30 to 50% CH2Cl2: hexane) followed by titration with diethyl ether to give 5-bromo-N-(1-(4-chlorophenylamino)-2-(naphthalen-1-yl)-2-oxoethyl)picolinamide (Compound-1, 352 mg, 37%). 1H NMR (300 MHz, CDCl3): δ=8.83 (d, J=8.7 Hz, 1H), 8.50 (d, J=1.5 Hz, 1H), 8.46 (d, J=9.6 Hz, 1H), 8.39 (dd, J=1.2, 7.2 Hz, 1H), 8.07-8.03 (m, 2H), 7.93 (dd, J=2.4, 8.7 Hz, 1H), 7.89 (d, J=7.5 Hz, 1H), 7.68-7.63 (m, 1H), 7.56 (t, J=7.8 Hz, 2H), 7.16 (d, J=8.7 Hz, 2H), 7.09-7.03 (m, 1H), 6.82 (d, J=9.0 Hz, 2H) 5.41 (d, J=8.1 Hz, 1H).

後処理

  1. temperaturecooled to 0° C
  2. customto react for 1 hour
  3. customThe reaction was quenched with water
  4. extractionthe product was extracted with ethyl acetate
  5. dry with materialThe organic solution was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated onto silica gel
  8. customThe product was purified by auto flash column chromatography (30 to 50% CH2Cl2: hexane)

出典と根拠

ORDレコード
ord-730f164881394cd7869c2ba51c03bab7
出典データセット
uspto-grants-2012_05
特許番号
US08168795B2

反応ノート

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