2-Fluoro-4-nitrophenol → 1-(2-(6-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)ethyl)pyrrolidin-2-one

HRID 1400907노트

반응식

HRID 1400907 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:16]=[CH:15][C:14]([CH2:17][CH2:18][N:19]4[CH2:23][CH2:22][CH2:21][C:20]4=[O:24])=[CH:13][CH:12]=3)[S:10][C:3]=12.[F:25][C:26]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:27]=1[OH:35].C(=O)([O-])[O-].[K+].[K+]>C1(OC2C=CC=CC=2)C=CC=CC=1>[F:25][C:26]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:27]=1[O:35][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:16]=[CH:15][C:14]([CH2:17][CH2:18][N:19]4[CH2:23][CH2:22][CH2:21][C:20]4=[O:24])=[CH:13][CH:12]=3)[S:10][C:3]=12

참가 물질

5

반응물 3

HCID 98252-Fluoro-4-nitrophenol2회HCID 11430Potassium Carbonate2회HCID 584746401-(2-(6-(7-Chlorothieno[3,2-b]pyridin-2-yl)pyridin-3-yl)ethyl)pyrrolidin-2-one

생성물 1

HCID 584745171-(2-(6-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)ethyl)pyrrolidin-2-one수율 47%

시약·촉매·용매 1

HCID 7583Diphenyl Ether용매

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온도
200 °C

실험 절차

To chlorothienopyridine 292 (1.2 g, 3.4 mmol) in diphenyl ether (20 mL) was added 2-fluoro-4-nitrophenol (1.58 g, 10.1 mmol) and potassium carbonate (2.32 g, 16.8 mmol) and the resultant mixture was heated to 200° C. for 10 h. Extra 2-fluoro-4-nitrophenol (1.58 g, 10.1 mmol) and potassium carbonate (2.32 g, 16.8 mmol) were added and the mixture was heated at 200° C. for a further 6 h. The mixture was cooled to RT, partitioned between ethyl acetate and 1M aqueous NaOH then filtered through celite. The organic phase was collected, washed with water and brine, dried (anhydrous MgSO4), filtered and concentrated. The residue was purified by silica gel chromatography (10% methanol/ethyl acetate) to afford title compound 293 (0.76 g, 47% yield), contaminated with ˜10% starting material 292, as a yellow solid. MS (M+H): 479.5

후처리

  1. temperatureThe mixture was cooled to RT
  2. custompartitioned between ethyl acetate and 1M aqueous NaOH
  3. filtrationthen filtered through celite
  4. customThe organic phase was collected
  5. washwashed with water and brine
  6. dry with materialdried (anhydrous MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (10% methanol/ethyl acetate)

출처 및 근거

ORD 기록
ord-b718626258ad469aaa983e7d8b29cab0
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906852B2

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