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

HRID 55861노트

반응식

HRID 55861 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-959ad8dfe6724d83b24fbb5c45a759ae
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09433622B2

반응 노트

불러오는 중…