Acetonitrile → HCID 68283437、化合物

HRID 624033ノート

反応式

HRID 624033 の反応式
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].Cl[CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=1)=[O:12].C([O-])([O-])=O.[Cs+].[Cs+].CC#N>C(Cl)Cl>[F:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:11](=[O:12])[CH2:10][N:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]2)=[N:15][CH:16]=1

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 229347512-Chloro-N-(5-fluoro-2-pyridinyl)acetamide

生成物 1

HCID 68283437HCID 68283437、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

A flask was charged with 4-nitro-1H-pyrazole (230 mg, 2.03 mmol), 2-chloro-N-(5-fluoropyridin-2-yl)acetamide (2.24 mmol), Cs2CO3 (729 g, 2.24 mmol) and MeCN (11.5 mL). The resulting reaction mixture was stirred at reflux (80° C.) for 2 h, then allowed to reach rt. The mixture was diluted with DCM, filtered, the filter cake was washed with DCM. The filtercake was redisolved in DCM and water, the org. layer was separated and the aq. layer was extracted with DCM (2×). The combined org. layers were washed with brine, dried (MgSO4), filtered and concentrated to yield N-(5-fluoropyridin-2-yl)-2-(4-nitro-1H-pyrazol-1-yl)acetamide as a crude which was used in the next step without further purification. LC-MS conditions A: tR=0.67 min, [M+H]+=266.32.

後処理

  1. customThe resulting reaction mixture
  2. customto reach rt
  3. filtrationfiltered
  4. washthe filter cake was washed with DCM
  5. customlayer was separated
  6. extractionthe aq. layer was extracted with DCM (2×)
  7. washlayers were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-7ecb42fd55c246a98eede5c3cc12ce2e
出典データセット
uspto-grants-2016_04
特許番号
US09303023B2

反応ノート

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