Nitrogen → 2-(2-Methyl-[1,3]dioxolan-2-yl)-6-(4-nitro-pyrazol-1-ylmethyl)-pyridine

HRID 2064967ノート

反応式

HRID 2064967 の反応式
N#N.[CH3:3][C:4]1([C:9]2[N:14]=[C:13]([CH2:15]OS(C)(=O)=O)[CH:12]=[CH:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.[N+:21]([C:24]1[CH:25]=[N:26][NH:27][CH:28]=1)([O-:23])=[O:22].C([O-])([O-])=O.[K+].[K+].[I-]>CC(C)=O>[CH3:3][C:4]1([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([CH2:15][N:26]3[CH:25]=[C:24]([N+:21]([O-:23])=[O:22])[CH:28]=[N:27]3)[N:14]=2)[O:5][CH2:6][CH2:7][O:8]1

参加物

7

反応物 5

HCID 947Nitrogen2 回HCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 30165Iodide IonHCID 86649482Methanesulfonic acid 6-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-ylmethyl ester

生成物 1

HCID 669289362-(2-Methyl-[1,3]dioxolan-2-yl)-6-(4-nitro-pyrazol-1-ylmethyl)-pyridine

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methanesulfonic acid 6-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-ylmethyl ester (273 mg, 1.00 mmol) in acetone (4.0 mL) was added, under inert atmosphere (N2) to a solution of 4-nitro-1H-pyrazole (115 mg, 1.00 mmol) in acetone (4.0 mL). K2CO3 (698 mg, 5.00 mmol) and TBA iodide (64 mg, 0.20 mmol) were added and the reaction mixture was stirred at rt for 5 h. The solvent was removed under reduced pressure. Water (10 mL) and EA (10 mL) were added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (30:10 to 50:50 hept-EA) gave the title compound as a pale yellow oil. LC-MS-conditions 02: tR=0.87 min; [M+H]+=291.27.

後処理

  1. customThe solvent was removed under reduced pressure
  2. additionWater (10 mL) and EA (10 mL) were added
  3. extractionThe aq. layer was extracted with EA (10 mL)
  4. dry with materialextracts were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (30:10 to 50:50 hept-EA)

出典と根拠

ORDレコード
ord-c16fb77f6c534b768e0753b8fdedaa8e
出典データセット
uspto-grants-2012_10
特許番号
US08288419B2

反応ノート

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