Potassium Carbonate → methyl 1-((4-methoxyphenyl)methyl)-1H-indazole-3-carboxylate

HRID 1372788

반응식

HRID 1372788 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]1.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]2)=[CH:18][CH:17]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 657476methyl 1H-indazole-3-carboxylate

생성물 1

HCID 17859014methyl 1-((4-methoxyphenyl)methyl)-1H-indazole-3-carboxylate수율 25%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

Methyl 3-indazolylcarboxylate (2.0 g, 11.4 mmol) was dissolved in DMF (20 ml). To the resulting solution were added 4-methoxybenzyl chloride (1.7 ml, 12.5 mmol) and potassium carbonate (2.35 g, 17.0 mmol). The resulting mixture was stirred at 80° C. for 15 hours. After cooling, the reaction mixture was poured in water (50 ml), followed by extraction with ethyl acetate (200 ml). The extract was washed with saturated brine (2×100 ml), dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (4:1) eluate fractions, methyl 1-(4-methoxybenzyl)-3-indazolylcarboxylate (polar fractions, 838 mg, 25%) was obtained as a pale yellow oil and 2(4-methoxybenzyl) isomer (non-polar fractions, 500 mg, 15%) was obtained as a pale yellow oil.

후처리

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate (200 ml)
  3. washThe extract was washed with saturated brine (2×100 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (4:1) eluate fractions

출처 및 근거

ORD 기록
ord-c7002c1244cd462b8493fd8eb5681b9c
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157487B2

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