Acetic Anhydride → 1-(5-Bromo-4-fluoroindazol-1-yl)ethanone

HRID 2400942ノート

反応式

HRID 2400942 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[C:3]=1[F:13].C(OC(=O)C)(=O)C.C([O-])(=O)C.[K+].C1OCCOCCOCCOCCOCCOC1.[N:44](OCCC(C)C)=O>ClCCCl>[Br:1][C:2]1[C:3]([F:13])=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]([C:9](=[O:11])[CH3:10])[N:44]=[CH:12]2

参加物

7

反応物 5

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 67123438N-(4-Bromo-3-fluoro-2-methylphenyl)acetamide

生成物 1

HCID 671234961-(5-Bromo-4-fluoroindazol-1-yl)ethanone

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
65 °C

実験手順

N-(4-Bromo-3-fluoro-2-methylphenyl)acetamide (36 mmol) was suspended in 1,2 dichloroethane (150 mL) and acetic anhydride (108 mmol), potassium acetate (74 mmol), 18-Crown-6 (1.4 mmol) and isopentyl nitrite (79 mmol) were added sequentially. The mixture was heated at 65° C. for 24 h, cooled to rt and washed with sat. NaHCO3. The organic layer was dried (Na2SO4) and concentrated and the residue was purified by flash chromatography (0-20% EtOAc/hexanes). 1-(5-Bromo-4-fluoroindazol-1-yl)ethanone was obtained as a brown solid.

後処理

  1. temperaturecooled to rt
  2. washwashed with sat. NaHCO3
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customthe residue was purified by flash chromatography (0-20% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-8abd23e0bbd14ffaa927ae166b7db053
出典データセット
uspto-grants-2014_08
特許番号
US08796256B2

反応ノート

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