반응 #1135845

반응 방정식

5-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide

3,4-dihydro-2H-pyran

NaHCO3

→

5-iodo-N-methoxy-N-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxamide

수율 92.0%

용매

DCM

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도to reflux for 5 hours
3. 3
   기타the layers were separated
4. 4
   추출the aqueous layer was extracted with DCM
5. 5
   세척The combined organic layers were washed with 5% aqueous citric acid and brine
6. 6
   건조dried over MgSO4
7. 7
   농축concentrated
8. 8
   기타The crude product was purified on a silica gel column (100% EtOAc→3:97 MeOH:DCM)

실험 절차

A mixture of 5-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide (X) (16.5 g, 50 mmol), 3,4-dihydro-2H-pyran (10.3 mL, 113 mmol) and PPTS (0.12 g, 0.6 mmol) in DCM was heated to reflux for 5 hours. The solution was poured into a saturated NaHCO3 solution, the layers were separated, and the aqueous layer was extracted with DCM. The combined organic layers were washed with 5% aqueous citric acid and brine, dried over MgSO4, and concentrated. The crude product was purified on a silica gel column (100% EtOAc→3:97 MeOH:DCM) to provide 5-iodo-N-methoxy-N-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxamide (XI) as a white viscous oil (19.1 g, 46 mmol, 92% yield). 1H NMR (DMSO-d6) δ ppm 1.28-1.84 (m, 6H), 3.43 (s, 3H), 3.60-4.04 (s, 5H), 5.86-6.08 (m, 1H), 7.45-7.87 (m, 2H), 8.39 (s, 1H); ESIMS found for C15H18IN3O3 m/z 416 (M+H).

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