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

HRID 571102노트

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HRID 571102 반응식
[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

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 247212012,3-Dimethyl-4-fluoronitrobenzeneHCID 178507942HCID 178507942, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
75 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-7b22dc1deb2b434bab6d460d4a591949
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024041B2

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