Tetrabutylammonium Fluoride → HCID 90460860, compound

HRID 1053637Notes

Reaction equation

HRID 1053637 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)[N:13]=[C:12]2[CH:24]=[O:25])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)[N:13]=[C:12]2[CH:24]=[O:25]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90460795HCID 90460795, compound

Product 1

HCID 90460860HCID 90460860, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R/S) 5-(tert-butyldimethylsilyloxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carbaldehyde (150 mg, 0.42 mmol, 1.00 equiv) and TBAF (800 mg, 800.00 mmol, 1922.79 equiv) in THF (5 mL) was stirred at room temperature for 2 h. The reaction mixture was diluted with 10 mL of H2O and then extracted with 3×20 mL of dichloromethane. The combined organic layers was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 10-20% of ethyl acetate in petroleum ether to give 0.1 g (98%) of (R/S) 5-hydroxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carbaldehyde as an off-white solid. LCMS (method A, ESI): RT=1.33 min, m/z=246.0 [M+H]+.

Workup

  1. extractionextracted with 3×20 mL of dichloromethane
  2. dry with materialThe combined organic layers was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified on a silica gel column
  5. washeluted with 10-20% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-c7fdffaa84b34a50ae3a670f5b181e6d
Source dataset
uspto-grants-2016_07
Patent number
US09394258B2

Reaction notes

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