Potassium Carbonate → 4-(2,3-Dimethyl-4-nitrophenoxy)pyridin-2-amine

HRID 571102ノート

反応式

HRID 571102 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=1.F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([CH3:19])[C:11]=1[CH3:20].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH3:20][C:11]1[C:12]([CH3:19])=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=1[O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 247212012,3-Dimethyl-4-fluoronitrobenzeneHCID 178507942HCID 178507942、化合物

生成物 1

HCID 585648204-(2,3-Dimethyl-4-nitrophenoxy)pyridin-2-amine

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
75 °C

実験手順

To a stirred solution of 2-aminopyridin-4-ol (600 mg, 5.5 mmol) and 1-fluoro-2,3-dimethyl-4-nitrobenzene (570 mg, 3.37 mmol) in DMSO (4.0 mL) was added K2CO3 (1.00 g, 7.20 mmol) and the reaction mixture heated to 75° C. for 3 days. The resulting mixture was cooled to RT and was partitioned between water (50 mL) and EtOAc (75 mL). The aq layer was separated and extracted with EtOAc (75 mL) and the combined organic extracts were washed with water (3×50 mL) and brine (50 mL) and then dried and evaporated in vacuo. The residue was recrystallized from DCM to afford the title compound, Intermediate C2, as a tan solid (25 mg, 28%): Rt 1.40 min (Method 2); m/z 260 (M+H)+ (ES+).

後処理

  1. temperatureThe resulting mixture was cooled to RT
  2. customwas partitioned between water (50 mL) and EtOAc (75 mL)
  3. customThe aq layer was separated
  4. extractionextracted with EtOAc (75 mL)
  5. washthe combined organic extracts were washed with water (3×50 mL) and brine (50 mL)
  6. customdried
  7. customevaporated in vacuo
  8. customThe residue was recrystallized from DCM

出典と根拠

ORDレコード
ord-7b22dc1deb2b434bab6d460d4a591949
出典データセット
uspto-grants-2015_05
特許番号
US09024041B2

反応ノート

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