Ethanol → 4-(3'-Chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-phenylamine

HRID 1632030노트

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HRID 1632030 반응식
C(O)C.[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=3)[C:12]=2[F:29])[CH:8]=[CH:9][CH:10]=1>[Fe].O>[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([NH2:26])=[CH:24][CH:25]=3)[C:12]=2[F:29])[CH:8]=[CH:9][CH:10]=1

참가 물질

5

반응물 2

HCID 702EthanolHCID 580201863'-Chloro-2-fluoro-6-methoxy-3-(4-nitro-benzyl)-biphenyl

생성물 1

HCID 580200234-(3'-Chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-phenylamine수율 79%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

반응 조건

온도
85 °C

실험 절차

In an 18 mL vial equipped with a stir bar was placed iron powder (179 mg, 3.20 mmol), ethanol (5.0 mL) and water (1.2 mL). The mixture was heated to 85° C. in an oil bath and then the above product 3′-Chloro-2-fluoro-6-methoxy-3-(4-nitro-benzyl)-biphenyl (6) (340 mg, 0.914 mmol) was added and the reaction was continued at 85° C. for 2 hours. The reaction mixture was cooled to room temperature and filtered through Celite. To the filtrate was added water (50 mL) and extractions were performed with ethyl acetate (2×60 mL). The organic portions were combined, washed with brine (50 mL), dried (MgSO4) and concentrated to produce 245 mg of 4-(3′-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-phenylamine (I-35) as a yellow, viscous oil in 79% yield. MS (APCI+): 342.0 (M+1).

후처리

  1. customIn an 18 mL vial equipped with a stir bar
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered through Celite
  4. additionTo the filtrate was added
  5. extractionwater (50 mL) and extractions
  6. washwashed with brine (50 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8dbc857c3542494696f8b7de4e912620
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791267B2

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