4-Chloro-3-nitropyridine → 4-Cyclohexenyl-3-nitropyridine

HRID 69874노트

반응식

HRID 69874 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[C:11]1(B(O)O)[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.COCCOC>[C:11]1([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=1

참가 물질

5

반응물 2

HCID 27357814-Chloro-3-nitropyridineHCID 38629021-Cyclohexenylboronic acid

생성물 1

HCID 690448894-Cyclohexenyl-3-nitropyridine수율 82%

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

A solution of 4-chloro-3-nitro pyridine (1 eq.), cyclohexenyl boronic acid (1.7 eq.), and Pd(dppf)Cl2—CH2Cl2 (0.05 eq) in 3:1 DME/2M Na2CO3, at a concentration of 0.1 M was heated at 95° C. for 16 hours. Upon cooling the reaction was partitioned between EtOAc and H2O, was washed with NaCl(sat.), dried over MgSO4, was filtered and the volatiles were removed in vacuo. The material was purified by SiO2 chromatography (20% EtOAc/hexanes eluant) to yield 4-cyclohexenyl-3-nitropyridine (82%). LCMS (m/z): 205.0 (MH+); LC Rt=3.84 min.

후처리

  1. temperatureUpon cooling the reaction
  2. customwas partitioned between EtOAc and H2O
  3. washwas washed with NaCl(sat.)
  4. dry with materialdried over MgSO4
  5. filtrationwas filtered
  6. customthe volatiles were removed in vacuo
  7. customThe material was purified by SiO2 chromatography (20% EtOAc/hexanes eluant)

출처 및 근거

ORD 기록
ord-e9a23e06244e4836baba6265ef0bfc7a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822497B2

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