3-Tert-butyl-isoxazole-5-carboxylic acid [3-nitro-4-trifluoromethyl-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide → 2-(3-tert-butyl-isoxazol-5-yl)-7-trifluoromethyl-5-(2-trifluoromethyl-phenyl)-1H-imidazo[4,5-b]pyridine

HRID 1191210노트

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HRID 1191210 반응식
[N+:1]([C:4]1[C:5]([NH:24][C:25]([C:27]2[O:31][N:30]=[C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:28]=2)=O)=[N:6][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:23])([F:22])[F:21])=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])([O-])=O>CC(O)=O.[Fe]>[C:32]([C:29]1[CH:28]=[C:27]([C:25]2[NH:1][C:4]3[C:5]([N:24]=2)=[N:6][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:21])([F:23])[F:22])=[CH:8][C:9]=3[C:10]([F:13])([F:12])[F:11])[O:31][N:30]=1)([CH3:33])([CH3:35])[CH3:34]

참가 물질

4

반응물 1

HCID 866574113-Tert-butyl-isoxazole-5-carboxylic acid [3-nitro-4-trifluoromethyl-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide

생성물 1

HCID 1360731612-(3-tert-butyl-isoxazol-5-yl)-7-trifluoromethyl-5-(2-trifluoromethyl-phenyl)-1H-imidazo[4,5-b]pyridine

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

A solution of 3-tert-butyl-isoxazole-5-carboxylic acid [3-nitro-4-trifluoromethyl-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide (14.6 mg, 0.029 mmol, prepared as described in STEP E above) in AcOH (3 mL) was treated with iron powder (8.12 mg, 0.145 mmol), and the resulting mixture was stirred at 100° C. for 2 h and concentrated in vacuo. The residue was taken up in saturated aqueous NaHCO3 (30 mL) and extracted twice with EtOAc (25 mL). The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified on a 4-g SEPRA Si 50 SPE column (Flow rate=10 mL/min; Eluent=EtOAc-hexanes, 1:99 for 10 min, then 1:99 to 1:4 over 40 min) to yield 2-(3-tert-butyl-isoxazol-5-yl)-7-trifluoromethyl-5-(2-trifluoromethyl-phenyl)-1H-imidazo[4,5-b]pyridine as a white solid. 1H-NMR (400 MHz, CD3OD) δ: 7.77 (d, J=7.6 Hz, 1H), 7.63-7.69 (m, 1H), 7.58-7.62 (m, 2H), 7.52-7.58 (m, 1H), 7.26 (s, 1H), 1.33 (s, 9H). Mass Spectrum (LCMS, APCI pos.): Calculated for C21H16N4OF6: 455.1 (M+H); Measured: 455.1.

후처리

  1. concentrationconcentrated in vacuo
  2. extractionextracted twice with EtOAc (25 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on a 4-g SEPRA Si 50 SPE column (Flow rate=10 mL/min
  6. waitEluent=EtOAc-hexanes, 1:99 for 10 min

출처 및 근거

ORD 기록
ord-4d4bd718e3d746639590756081c569e7
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680098B2

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