7-硝基吲唑 → 7-硝基-1H-吲唑-1-羧酸叔丁酯

HRID 482343

反应方程式

HRID 482343 反应方程式
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][N:10]=[CH:9]2)([O-:3])=[O:2].[C:13](=O)([O:19]C(C)(C)C)[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(#N)C>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([C:13]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:19])[N:10]=[CH:9]2)([O-:3])=[O:2]

参与物

6

反应物 3

HCID 18937-硝基吲唑HCID 8471三乙胺HCID 10219638碳酸二叔丁酯

产物 1

HCID 156060217-硝基-1H-吲唑-1-羧酸叔丁酯收率 59%

试剂、催化剂与溶剂 2

HCID 142844-二甲氨基吡啶(DMAP)催化剂HCID 6342乙腈溶剂

实验过程

A solution of 7-nitro-1H-indazole (2.81 g, 17.23 mmol), di-tertbutyl carbonate (7.52 g, 34.5 mmol), triethylamine (4.81 mL, 34.5 mmol) and 4-dimethylamino-pyridine (2.11 g, 17.2 mmol) in anhydrous acetonitrile (100 mL) is stirred under nitrogen at ambient temperature for approximately 3 hrs. After removing the solvent in vacuo, the residue is partitioned between ethyl acetate and aqueous sodium hydrogen sulfate (1N). The organic layer is separated, washed with saturated aqueous brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The crude product is purified by chromatography on flash grade silica gel using DCM. Fractions containing the product are combined, concentrated in vacuo to a solid and dried under high vacuum to provide the title compound as a yellow solid (2.674 g, 10.16 mmol). 1H NMR (300 MHz, d6-DMSO) δ=1.55 (s, 9H); 7.58 (t, J=8.0 Hz, 1H); 8.20 (d, J=7.4 Hz, 1H); 8.30 (d, J=7.7 Hz, 1H); 8.67 (s, 1H), TLC: Rf =0.5 (DCM).

后处理

  1. customAfter removing the solvent in vacuo
  2. customthe residue is partitioned between ethyl acetate and aqueous sodium hydrogen sulfate (1N)
  3. customThe organic layer is separated
  4. washwashed with saturated aqueous brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by chromatography on flash grade silica gel
  9. additionFractions containing the product
  10. concentrationconcentrated in vacuo to a solid
  11. customdried under high vacuum

来源与证据

ORD记录
ord-b6abbb564f7b405db91470f74f1214ec
来源数据集
uspto-grants-1998_08
专利号
US05795887

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