2-Fluoro-4-nitrophenol → Methyl 7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carboxylate

HRID 500763노트

반응식

HRID 500763 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[S:10][C:3]=12.[F:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[OH:25].C([O-])([O-])=O.[K+].[K+]>O(C1C=CC=CC=1)C1C=CC=CC=1.CCOC(C)=O>[F:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[O:25][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[S:10][C:3]=12

참가 물질

6

반응물 3

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 59424429Methyl 7-chlorothieno[3,2-B]pyridine-2-carboxylate

생성물 1

HCID 59424450Methyl 7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carboxylate수율 59%

시약·촉매·용매 2

HCID 7583Diphenyl Ether용매HCID 8857Ethyl Acetate용매

반응 조건

온도
180 °C

실험 절차

A mixture of 37 (4.0 g, 17.6 mmol), 2-fluoro-4-nitrophenol (5.5 g, 35.0 mmol) and K2CO3 (12.1 g, 87.5 mmol) in Ph2O was heated at 180° C. for 5 hours. The mixture was cooled to room temperature, diluted with EtOAc and washed with water. The organic phase was collected, dried over anhydrous sodium sulfate and the solvents were removed under reduced pressure. The residue was purified by flash chromatography using hexane—AcOEt (70:30) as an eluent. The product from the column was re-crystallized from a mixture of ethyl acetate-hexanes to afford 38 (3.6 g, 59% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.69 (d, J=5.2 Hz, 1H), 8.47 (dd, J=2.4 and 10.0 Hz, 1H), 8.27 (s, 1H), 7.77 (dd, J=8.0 and 9.2 Hz, 1H), 7.06 (dd, J=0.8 and 5.2 Hz, 1H), 3.93 (s, 3H).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water
  3. customThe organic phase was collected
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvents were removed under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. customThe product from the column was re-crystallized from a mixture of ethyl acetate-hexanes

출처 및 근거

ORD 기록
ord-24d4670dd2874471ab5ae527c5809161
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772247B2

반응 노트

불러오는 중…