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

HRID 69874ノート

反応式

HRID 69874 の反応式
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

参加物

5

反応物 2

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

生成物 1

HCID 690448894-Cyclohexenyl-3-nitropyridine収率 82%

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e9a23e06244e4836baba6265ef0bfc7a
出典データセット
uspto-grants-2014_09
特許番号
US08822497B2

反応ノート

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