S-ethyl 2-bromopyridine-4-carbothioate → 2-(2-Bromopyridine-4-carbonyl)-6-fluorobenzonitrile

HRID 1662205ノート

反応式

HRID 1662205 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([C:8](=[O:12])SCC)[CH:5]=[CH:4][N:3]=1.[I-].[C:14]([C:16]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=1[Zn+])#[N:15]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([C:17]2[CH:18]=[CH:19][CH:20]=[C:21]([F:22])[C:16]=2[C:14]#[N:15])=[O:12])[CH:5]=[CH:4][N:3]=1

参加物

5

反応物 2

HCID 58579502S-ethyl 2-bromopyridine-4-carbothioateHCID 178510276HCID 178510276、化合物

生成物 1

HCID 585795282-(2-Bromopyridine-4-carbonyl)-6-fluorobenzonitrile収率 60.9%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

実験手順

To a degassed solution of S-ethyl 2-bromopyridine-4-carbothioate (5.0 g, 20.3 mmol) in anhydrous toluene (50 mL), Pd(OAc)2 (0.82 g, 3.66 mmol) was added followed by dropwise addition of 2-cyano-3-fluorophenylzinc iodide (0.5M in THF, 36.6 mL, 18.3 mmol). The reaction mixture was stirred at room temperature for 2 hours with continued bubbling of nitrogen. Water (50 mL) and saturated aqueous NH4Cl (100 mL) were added and the resulting mixture was extracted with ethyl acetate (2×200 mL). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography using a gradient of 25% to 100% ethyl acetate in hexanes to afford 3.4 g of the title compound (1.5 g, 27%).

後処理

  1. customwith continued bubbling of nitrogen
  2. additionWater (50 mL) and saturated aqueous NH4Cl (100 mL) were added
  3. extractionthe resulting mixture was extracted with ethyl acetate (2×200 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-f889585d78af4d4a81395297802d4fbb
出典データセット
uspto-grants-2011_10
特許番号
US08030500B2

反応ノート

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