(S)-3-fluoropyrrolidine → 5-Bromo-2-((S)-3-fluoro-pyrrolidin-1-yl)-nicotinonitrile

HRID 55860노트

반응식

HRID 55860 반응식
[Br:1][C:2]1[CH:3]=[N:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].[F:11][C@H:12]1[CH2:16][CH2:15][NH:14][CH2:13]1>CC#N>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:14]2[CH2:15][CH2:16][C@H:12]([F:11])[CH2:13]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

참가 물질

4

반응물 2

HCID 7016277(S)-3-fluoropyrrolidineHCID 848197325-Bromo-2-fluoropyridine-3-carbonitrile

생성물 1

HCID 903566975-Bromo-2-((S)-3-fluoro-pyrrolidin-1-yl)-nicotinonitrile

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

5-Bromo-2-fluoro-nicotinonitrile (4) (5.0 g, 24.9 mmol) and (S)-(+)-3-fluoropyrrolidine (3.3 g, 25.9 mmol) were dissolved in dry MeCN (100 mL). TEA (8.0 mL, 57.4 mol) was added and the mixture stirred at rt for 2 hours. The solvent was evaporated in vacuo and the residue partitioned between H2O (100 mL) and EtOAc (100 mL). The organic phase was washed with saturated brine solution (100 mL), then dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was dissolved in DCM (100 mL) and the solvent evaporated in vacuo. The title compound was obtained as an off-white solid (6.3 g, 94%); LCMS, Rt=2.86 min (MeOH-FA method), m/z 270, 272 (MH+).

후처리

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between H2O (100 mL) and EtOAc (100 mL)
  3. washThe organic phase was washed with saturated brine solution (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. dissolutionThe residue was dissolved in DCM (100 mL)
  8. customthe solvent evaporated in vacuo

출처 및 근거

ORD 기록
ord-90b3c37bfa2348d2a8da72af9a9b47bb
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09433622B2

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