Potassium Carbonate → 4-(2-Fluoro-4-nitrophenoxy)-2-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 2117166노트

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HRID 2117166 반응식
[CH3:1][C:2]1[NH:11][C:5]2[N:6]=[CH:7][CH:8]=[C:9]([OH:10])[C:4]=2[CH:3]=1.[F:12][C:13]1[CH:14]=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[CH:17][C:18]=1F.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[F:12][C:13]1[CH:14]=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[CH:17][C:18]=1[O:10][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:11][C:2]([CH3:1])=[CH:3][C:4]=12

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 178422234HCID 178422234, 화합물

생성물 1

HCID 210816374-(2-Fluoro-4-nitrophenoxy)-2-methyl-1H-pyrrolo[2,3-b]pyridine수율 46%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

A mixture of 2-methyl-1H-pyrrolo[2,3-b]pyridin-4-ol (90 mg, TFA salt, 0.34 mmol), 3,4-difluoronitrobenzene (0.05 mL) and potassium carbonate (100 mg, 0.72 mmol) in DMF (1 mL) was stirred at 50° C. for 2 h. The mixture was diluted with water and extracted with ethyl acetate (3×5 mL). The combined extracts were washed with water, dried (MgSO4) and concentrated in vacuo to afford the crude product, which was purified by preparative HPLC to give the title compound (45 mg, 46%). 1H NMR (CD3OD) δ 8.25 (dd, 2H, J=10.4, 2.6 Hz), 8.12 (m, 1H), 8.04 (d, 1H, J=5.5 Hz), 7.30 (t, 1H, J=8.3 Hz), 6.67 (d, 1H, J=5.5 Hz), 5.95 (s, 1H), 2.41 (s, 3H); MS(ESI+) m/z 288 (M+H)+.

후처리

  1. extractionextracted with ethyl acetate (3×5 mL)
  2. washThe combined extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto afford the crude product, which
  6. customwas purified by preparative HPLC

출처 및 근거

ORD 기록
ord-251d103fdcd14913a8fff803fe5553b3
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07439246B2

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