Tetrahydrofuran → 1-[5-Fluoro-8-(3-fluorophenyl)quinolin-7-yl]ethanamine

HRID 1192691노트

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HRID 1192691 반응식
[F:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([O-])(=O)C.[NH4+:26].[Na].O1CCCC1>CO.C(#N)C>[F:1][C:2]1[CH:11]=[C:10]([CH:12]([NH2:26])[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5360545SodiumHCID 583684731-[5-Fluoro-8-(3-fluorophenyl)quinolin-7-yl]ethanone

생성물 1

HCID 583685621-[5-Fluoro-8-(3-fluorophenyl)quinolin-7-yl]ethanamine

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매

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온도
65 °C

실험 절차

A mixture of 1-[5-fluoro-8-(3-fluorophenyl)quinolin-7-yl]ethanone (0.32 g, 1.1 mmol) and ammonium acetate (0.871 g, 11.3 mmol) in methanol (3.0 mL) and acetonitrile (3.0 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling to room temperature, to the resulting mixture was added 1.0 M sodium cyanoborohyride in tetrahydrofuran (2.8 mL, 2.8 mmol). The reaction was heated at 65° C. overnight, then cooled to room temperature and quenched with sat. NaHCO3 solution and extracted with dichloromethane. The combined extracts were dried over MgSO4 and evaporated to dryness. The residue was used directly in the next step. LCMS calculated for C17H15F2N2 (M+H)+: m/z=285.1; Found: 285.1.

후처리

  1. temperatureAfter cooling to room temperature, to the resulting mixture
  2. temperatureThe reaction was heated at 65° C. overnight
  3. temperaturecooled to room temperature
  4. customquenched with sat. NaHCO3 solution
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined extracts were dried over MgSO4
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-69f45e4ef9c0478c90ff58f7181934fa
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680108B2

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