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

HRID 660364

反応式

HRID 660364 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-aa78929fb88d4d59b52175c62d3f59eb
出典データセット
uspto-grants-2011_12
特許番号
US08084485B2

関連ノート

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