Water → 1-(3-methoxypropyl)-6-nitro-1H-indazole

HRID 660364

반응식

HRID 660364 반응식
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CS(O[CH2:18][CH2:19][CH2:20][O:21][CH3:22])(=O)=O.C([O-])([O-])=O.[K+].[K+].O>CC#N>[CH3:22][O:21][CH2:20][CH2:19][CH2:18][N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH:8]=[N:9]1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 242396-NitroindazoleHCID 116939633-Methoxypropyl methanesulfonate

생성물 1

HCID 596309911-(3-methoxypropyl)-6-nitro-1H-indazole수율 46%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

A mixture of 6-nitro-1H-indazole (50 g, 0.307 mol), 3-methoxypropyl methanesulfonate (54.3 g, 0.323 mol) and K2CO3 (127 g, 0.921 mol) in CH3CN (1.5 L) was heated at 60° C. overnight. Water (1 L) was added and the CH3CN was removed under reduced pressure and the aqueous residue was extracted with EtOAc (3×500 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel to give 1-(3-methoxypropyl)-6-nitro-1H-indazole (33 g, 46% yield). 1H NMR (400 MHz, CDCl3): δ8.47 (s, 1H), 8.13 (s, 1H), 8.01-7.99 (dd, J=8.8, 2.0 Hz, 1H), 7.83-7.81 (d, J=8.8 Hz, 1H), 4.61-4.57 (t, J=6.4 Hz, 2H), 3.29 (s, 3H), 3.26-3.23 (t, J=5.6 Hz, 2H), 2.23-2.17 (m, 2H).

후처리

  1. customthe CH3CN was removed under reduced pressure
  2. extractionthe aqueous residue was extracted with EtOAc (3×500 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-aa78929fb88d4d59b52175c62d3f59eb
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084485B2

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