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

HRID 55861ノート

反応式

HRID 55861 の反応式
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[C:6]([CH:9]=1)[C:7]#[N:8].Cl.[F:12][C@H:13]1[CH2:17][CH2:16][NH:15][CH2:14]1.CCN(C(C)C)C(C)C>CC#N>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:15]2[CH2:16][CH2:17][C@H:13]([F:12])[CH2:14]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 16217739(s)-3-Fluoropyrrolidine hydrochlorideHCID 219482695-Bromo-2-chloronicotinonitrile

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-chloro-nicotinonitrile (6) (5.0 g, 23.0 mmol) was dissolved in MeCN (100 mL). (S)-3-Fluoropyrrolidine hydrochloride (5.7 g, 53.0 mmol) and DIPEA (12.0 mL, 68.9 mmol) were added and the mixture was stirred at reflux for 1 hour. The solvent was evaporated in vacuo and the residue partitioned between EtOAc (100 mL) and H2O (50 mL). The layers were separated and the organic phase washed with saturated brine solution (50 mL), then dried (MgSO4), filtered and the solvent evaporated in vacuo. The title compound was obtained as an off-white solid (6.2 g, 100%); LCMS, Rt=2.91 min (MeOH-FA method), m/z 270, 272 (MH+).

後処理

  1. temperatureat reflux for 1 hour
  2. customThe solvent was evaporated in vacuo
  3. customthe residue partitioned between EtOAc (100 mL) and H2O (50 mL)
  4. customThe layers were separated
  5. washthe organic phase washed with saturated brine solution (50 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo

出典と根拠

ORDレコード
ord-959ad8dfe6724d83b24fbb5c45a759ae
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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