Tetrabutylammonium Fluoride → HCID 68283545, compound

HRID 1527279Notes

Reaction equation

HRID 1527279 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:9]2[C:5](=[C:6]([C:22](=[O:24])[CH3:23])[N:7](COCC[Si](C)(C)C)[N:8]=2)[CH:4]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[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]=[C:6]2[C:22](=[O:24])[CH3:23]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68283542HCID 68283542, compound

Product 1

HCID 68283545HCID 68283545, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

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 1-(5,6-dimethoxy-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-3-yl]ethanone (200 mg, 0.57 mmol) in THF (6 mL) was added a 1M solution in THF of TBAF (2.85 mL, 2.85 mmol), and the mixture was heated to reflux for 16 h. The reaction mixture was then diluted with EtOAc and successively washed with water and brine, then dried (Phase separator) and evaporated. The crude product was purified by preparative HPLC (Waters Sunfire, C18-ODB, 5 μm, 30×100 mm, flow: 40 mL/min, eluent: 5-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA) to give after lyophilization of the purified fractions the title compound. MS (LC-MS): 221 [M+H]+; tR (HPLC conditions k): 2.61 min.

Workup

  1. customThe title compound was prepared in a similar manner
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 16 h
  4. washsuccessively washed with water and brine
  5. customdried (Phase separator)
  6. customevaporated
  7. customThe crude product was purified by preparative HPLC (Waters Sunfire, C18-ODB, 5 μm, 30×100 mm, flow: 40 mL/min, eluent: 5-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA)

Sources & evidence

ORD record
ord-6956fb4538d54221970018f96e8d1c2c
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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