Ethyl Acetate → HCID 68284656, compound

HRID 1527277Notes

Reaction equation

HRID 1527277 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][N:7]=[CH:6]2.C1(C(N)C2CCCCC2)CCCCC1.[CH3:28][Si:29]([CH2:32][CH2:33][O:34][CH2:35]Cl)([CH3:31])[CH3:30].CCOC(C)=O>C1COCC1>[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:9]2[C:5](=[CH:6][N:7]([CH2:35][O:34][CH2:33][CH2:32][Si:29]([CH3:31])([CH3:30])[CH3:28])[N:8]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 10774245alpha-CyclohexylcyclohexanemethanamineHCID 198391985,6-Dimethoxy-1H-indazole

Product 1

HCID 68284656HCID 68284656, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared in a similar manner as described by G. Luo et al., J. Org. Chem. 2006, 71, 5392-5395: To a solution of 5,6-dimethoxyindazole [7746-30-7] (356 mg, 2.00 mmol) in THF (20 mL) was added dicyclohexylmethylamine (0.51 mL, 2.40 mmol) followed by SEM-Cl (0.43 mL, 2.40 mmol). The mixture was stirred at RT for 24 h, followed by dilution with EtOAc and quench with 1N aqueous NaOH solution. The layers were separated and the organic layer was washed with water and brine, then dried (Phase separator) and evaporated. The residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 4:1 to 1:1) to separate from the regioisomer 5,6-dimethoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole and to provide the title compound. TLC, Rf (c-hexane/EtOAc 1:1)=0.37; MS (LC/MS): 309 [M+H; tR (HPLC conditions k): 3.70 min.

Workup

  1. customThe title compound was prepared in a similar manner
  2. customquench with 1N aqueous NaOH solution
  3. customThe layers were separated
  4. washthe organic layer was washed with water and brine
  5. customdried (Phase separator)
  6. customevaporated
  7. customThe residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 4:1 to 1:1)
  8. customto separate from the regioisomer 5,6-dimethoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole

Sources & evidence

ORD record
ord-bb3d49c2023b4ad298c3c62c200ed703
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…