Acrylonitrile → (S)-3-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yl)acrylonitrile

HRID 874069노트

반응식

HRID 874069 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C@@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[CH3:13])[CH:7]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.[C:43](#[N:46])[CH:44]=[CH2:45]>CC#N.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:13][N:9]1[CH2:10][CH2:11][CH2:12][C@H:8]1[C:6]1[CH:7]=[C:2]([CH:45]=[CH:44][C:43]#[N:46])[CH:3]=[N:4][CH:5]=1

참가 물질

7

반응물 4

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 10633832Pyridine, 3-bromo-5-[(2S)-1-methyl-2-pyrrolidinyl]-

생성물 1

HCID 86659932(S)-3-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yl)acrylonitrile수율 71.1%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매

실험 절차

A mixture of (S)-3-bromo-5-(1-methylpyrrolidin-2-yl)pyridine (preparation 1) (300 mg, 1.24 mmol), palladium (II) acetate (14 mg, 0.06 mmol), tri(o-tolyl)phosphine (75 mg, 0.25 mmol) and triethylamine (0.35 mL, 2.48 mmol) in MeCN (10 mL) was degassed by bubbling argon through. Acrylonitrile (0.12 mL, 1.87 mmol) was then added and the reaction mixture heated at reflux temperature for 18 hours. The reaction mixture was cooled to room temperature, filtered through Celite, and the solvents evaporated to give a brown solid. The crude product was purified by flash chromatography (2% [20% ammonia in MeOH] in DCM) to give the title compound as a red-brown oil (188 mg, 71%, mixture of cis and trans isomers).

후처리

  1. customwas degassed
  2. customby bubbling argon through
  3. temperaturethe reaction mixture heated
  4. temperatureat reflux temperature for 18 hours
  5. filtrationfiltered through Celite
  6. customthe solvents evaporated
  7. customto give a brown solid
  8. customThe crude product was purified by flash chromatography (2% [20% ammonia in MeOH] in DCM)

출처 및 근거

ORD 기록
ord-d47365aea8fe49dc9f7d4fc444655bff
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980276B2

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