4-Chloroaniline → HCID 50943107, 화합물

HRID 1920083노트

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HRID 1920083 반응식
[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

참가 물질

6

반응물 3

HCID 78124-ChloroanilineHCID 24819Phosphorus pentachlorideHCID 58149557HCID 58149557, 화합물

생성물 1

HCID 50943107HCID 50943107, 화합물수율 37%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-730f164881394cd7869c2ba51c03bab7
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168795B2

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