Bromobenzene → 2-Methyl-6-[3-(1-phenylpiperidin-4-ylidene)prop-1-ynyl]pyridine

HRID 1895965

反応式

HRID 1895965 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[N:3]=1.Br[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:12][CH2:13][N:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][CH2:16]2)[N:3]=1

参加物

6

反応物 3

HCID 7961BromobenzeneHCID 10796Cesium carbonateHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

生成物 1

HCID 251838262-Methyl-6-[3-(1-phenylpiperidin-4-ylidene)prop-1-ynyl]pyridine収率 100%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 634876Binap, (A+-)-触媒

反応条件

温度
110 °C

実験手順

A mixture of the compound of Example 3 (0.22 g, 1.04 mmol), bromobenzene (0.17 g, 1.04 mmol), cesium carbonate (0.68 g, 2.1 mmol), BINAP (0.031 g, 0.05 mmol), palladium(II)acetate (0.01 mg, 0.05 mmol), in anhydrous and degassed toluene (10 mL) was heated at 110° C. under a nitrogen atmosphere for 12 h in a sealed vessel. The reaction mixture was cooled, poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography (EtOAc—Petroleum Ether 2:8) affording the title product (0.30 g).

後処理

  1. customin anhydrous and degassed toluene (10 mL)
  2. temperatureThe reaction mixture was cooled
  3. additionpoured into water
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. customdried on Na2SO4
  7. customevaporated to dryness in vacuo
  8. customto afford a residue, which
  9. customwas purified by flash chromatography (EtOAc—Petroleum Ether 2:8)

出典と根拠

ORDレコード
ord-25430e53cc9c41d1a5f6276ae8efe333
出典データセット
uspto-grants-2013_08
特許番号
US08518916B2

関連ノート

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