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

HRID 55860ノート

反応式

HRID 55860 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-90b3c37bfa2348d2a8da72af9a9b47bb
出典データセット
uspto-grants-2016_09
特許番号
US09433622B2

反応ノート

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