Ammonium Chloride → (5-Fluoro-2-nitrophenyl)-(5-fluoropyridin-3-yl)amine

HRID 243102

반응식

HRID 243102 반응식
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[NH2:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([F:18])[CH:17]=1.F[C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[N+:27]([O-:29])=[O:28].[NH4+].[Cl-]>C1COCC1>[F:26][C:24]1[CH:23]=[CH:22][C:21]([N+:27]([O-:29])=[O:28])=[C:20]([NH:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([F:18])[CH:17]=2)[CH:25]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 679672,4-DifluoronitrobenzeneHCID 5744505-Fluoro-3-pyridinamineHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 68157752(5-Fluoro-2-nitrophenyl)-(5-fluoropyridin-3-yl)amine수율 34.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

LiHMDS (1.0M in THF, 10.0 mL, 10.0 mmol) was added dropwise to a stirred solution of 3-amino-5-fluoropyridine (588 mg, 5.26 mmol) in anhydrous THF (10 mL) under a nitrogen atmosphere at −78° C. After 20 min 2,4-difluoro-1-nitrobenzene (0.55 mL, 5.0 mmol) was added and stirring at −78° C. was continued for 1 h. The reaction mixture was poured into a saturated aqueous solution of NH4Cl (50 mL). The aqueous phase was extracted with EtOAc (×2) and the combined organic fractions washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-100% EtOAc in DCM) to afford the title compound as an orange solid (428 mg, 34%). LCMS (Method C): RT 3.27 min [M+H]+ 252.16

후처리

  1. extractionThe aqueous phase was extracted with EtOAc (×2)
  2. washthe combined organic fractions washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-100% EtOAc in DCM)

출처 및 근거

ORD 기록
ord-eedb0e9ffe5c4ad9a0ab08ec1655f8d0
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

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