Ammonium Chloride → (5-Fluoro-2-nitrophenyl)-(6-fluoropyridin-3-yl)amine

HRID 242989

反応式

HRID 242989 の反応式
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[F:11][C:12]1[N:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1.F[C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[N+:27]([O-:29])=[O:28].[NH4+].[Cl-]>C1COCC1>[F:26][C:24]1[CH:23]=[CH:22][C:21]([N+:27]([O-:29])=[O:28])=[C:20]([NH:18][C:15]2[CH:16]=[N:17][C:12]([F:11])=[CH:13][CH:14]=2)[CH:25]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 679672,4-DifluoronitrobenzeneHCID 8194405-Amino-2-fluoropyridineHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 68157161(5-Fluoro-2-nitrophenyl)-(6-fluoropyridin-3-yl)amine収率 91%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

LiHMDS (1.0M in THF, 5.0 mL, 5.0 mmol) was added dropwise to a stirred solution of 6-fluoropyridin-3-ylamine (294 mg, 2.63 mmol) in anhydrous THF (5 mL) under a nitrogen atmosphere at −78° C. After 30 min stirring at −78° C., a solution of 2,4-difluoro-1-nitrobenzene (275 μL, 2.50 mmol) in THF (5 mL) was added and stirring at −78° C. continued for 1 h. The solution was poured into an aqueous solution of NH4Cl and extracted with EtOAc (×3). The combined organic fractions were washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-100% DCM in cyclohexane) to afford the title compound as a yellow solid (571 mg, 91%). LCMS (Method C): RT 3.33 min [M+H]+ 252.1.

後処理

  1. stirringstirring at −78° C.
  2. waitcontinued for 1 h
  3. extractionextracted with EtOAc (×3)
  4. washThe combined organic fractions were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-100% DCM in cyclohexane)

出典と根拠

ORDレコード
ord-08c2135d81e74e8380c2aff864fe3759
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

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