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

HRID 1895965

반응식

HRID 1895965 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 634876Binap, (A+-)-촉매

반응 조건

온도
110 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-25430e53cc9c41d1a5f6276ae8efe333
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518916B2

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