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Dimethylformamide → 5-Ethyl-3-(piperidine-1-carbonyl)-thiophene-2-carbonitrile

HRID 1809083
ノート
印刷プレビュー

反応式

HRID 1809083 の反応式
Br[C:2]1[S:3][C:4]([CH2:15][CH3:16])=[CH:5][C:6]=1[C:7]([N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:8].[CH3:17][N:18](C=O)C>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:15]([C:4]1[S:3][C:2]([C:17]#[N:18])=[C:6]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])[CH:5]=1)[CH3:16]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 42643628(2-Bromo-5-ethyl-thiophen-3-yl)-piperidin-1-yl-methanone

生成物 1

HCID 426438755-Ethyl-3-(piperidine-1-carbonyl)-thiophene-2-carbonitrile

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒

反応条件

温度
100 °C

実験手順

(2-Bromo-5-ethyl-thiophen-3-yl)-piperidin-1-yl-methanone (0.1 g, 0.33 mmol) was dissolved in DMF (3 mL). Zinc cyanide (0.34 mmol) and tetrakis-(triphenylphosphine) palladium (0) (0.017 mmol) were added and the reaction mixture heated at 100° C. for 4 hours. The mixture was cooled to ambient temperature and the reaction quenched with a mixture of 5% aqueous sodium thiosulphate and saturated aqueous potassium carbonate (1:1, 5 mL) and extracted with diethyl ether. The organic solution was dried over magnesium sulphate, filtered and the solvent removed. The product was purified by HPLC, eluting with 20%-95% acetonitrile in water (0.1% formic acid) over 30 minutes. The fractions containing the desired product were concentrated under vacuum and freeze-dried to give the title compound (0.26 mg). LCMS m/z 249.14 [M+H]+ RT=9.75 min (Analytical Method 1). 1H NMR (400 MHz, CHCl3-d): δ 6.85 (t, 1H), 3.70 (m, 2H), 3.4 (m, 2H), 2.9 (m, 2H), 1.7 (m, 4H), 1.6 (s, 2H), 1.3 (t, 3H).

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe reaction quenched with a mixture of 5% aqueous sodium thiosulphate and saturated aqueous potassium carbonate (1:1, 5 mL)
  3. extractionextracted with diethyl ether
  4. dry with materialThe organic solution was dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent removed
  7. customThe product was purified by HPLC
  8. washeluting with 20%-95% acetonitrile in water (0.1% formic acid) over 30 minutes
  9. additionThe fractions containing the desired product
  10. concentrationwere concentrated under vacuum
  11. customfreeze-dried

出典と根拠

ORDレコード
ord-5a7370f56d1943b0a68b47d00c4f473c
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08362008B2

反応ノート

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