Bromide ion → 1-[2-(3-Nitro-pyrazol-1-ylmethyl)-oxazol-4-yl]-ethanone

HRID 2065075ノート

反応式

HRID 2065075 の反応式
N#N.[C:3]([C:6]1[N:7]=[C:8]([CH2:11]OS(C)(=O)=O)[O:9][CH:10]=1)(=[O:5])[CH3:4].C([O-])([O-])=O.[K+].[K+].[N+:23]([C:26]1[NH:30][N:29]=[CH:28][CH:27]=1)([O-:25])=[O:24].[Br-]>CC(C)=O>[N+:23]([C:26]1[CH:27]=[CH:28][N:29]([CH2:11][C:8]2[O:9][CH:10]=[C:6]([C:3](=[O:5])[CH3:4])[N:7]=2)[N:30]=1)([O-:25])=[O:24]

参加物

7

反応物 5

HCID 259Bromide ionHCID 947NitrogenHCID 11430Potassium CarbonateHCID 1234193-NitropyrazoleHCID 86649491Methanesulfonic acid 4-acetyl-oxazol-2-ylmethyl ester

生成物 1

HCID 669287371-[2-(3-Nitro-pyrazol-1-ylmethyl)-oxazol-4-yl]-ethanone

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

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 4-acetyl-oxazol-2-ylmethyl ester (70 mg, 0.32 mmol) in acetone (5.0 mL) was treated with K2CO3 (223 mg, 1.60 mmol) followed by 5-nitro-1H-pyrazole (37 mg, 0.32 mmol) and TBA bromide (21 mg, 0.06 mmol). The reaction mixture was stirred at rt until completion. The solvent was removed under reduced pressure and water (10 mL) followed by 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 (1:1 hept-EA) gave the title compound as a yellow solid. TLC: rf (EA)=0.50. LC-MS-conditions 02: tR=0.74 min; [M+H]+=237.31.

後処理

  1. customThe solvent was removed under reduced pressure and water (10 mL)
  2. additionwere 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 (1:1 hept-EA)

出典と根拠

ORDレコード
ord-4bb74ec2baa64a5983bdf9fd6eacc89f
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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