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

HRID 874069ノート

反応式

HRID 874069 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d47365aea8fe49dc9f7d4fc444655bff
出典データセット
uspto-grants-2015_03
特許番号
US08980276B2

反応ノート

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