Water → 2-Methyl-6-{3-[1-(5-nitrofuran-2-yl)piperidin-4-ylidene]prop-1-yn-1-yl}pyridine

HRID 1895995

반응식

HRID 1895995 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[O:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[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[O:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=3)[CH2:15][CH2:16]2)[N:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2335822-Bromo-5-nitrofuranHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

생성물 1

HCID 875509042-Methyl-6-{3-[1-(5-nitrofuran-2-yl)piperidin-4-ylidene]prop-1-yn-1-yl}pyridine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A suspension of the Compound of Example 3 (100 mg, 0.47 mmol), 2-bromo-5-nitrofuran (98 mg, 0.51 mmol) and potassium carbonate (72 mg, 0.52 mmol) in DMF (2 mL) was stirred at r.t. for 4 h. Afterwards, the reaction mixture was 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 eluting with Petroleum Ether-EtOAc 6:4 affording the title product (94 mg) as a yellow solid.

후처리

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. customdried on Na2SO4
  4. customevaporated to dryness in vacuo
  5. customto afford a residue, which
  6. customwas purified by flash chromatography
  7. washeluting with Petroleum Ether-EtOAc 6:4 affording the title product (94 mg) as a yellow solid

출처 및 근거

ORD 기록
ord-a048f82404cc49949b0f2bfa2399be70
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518916B2

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