Tetrabutylammonium Fluoride Trihydrate → HCID 136367317, compound

HRID 2234104Notes

Reaction equation

HRID 2234104 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][O:18][Si](C(C)(C)C)(C)C)[CH:15]=2)[CH:10]=[C:9]1[C:26]1[CH:31]=[C:30]([C:32]2[CH:37]=[C:36]([CH3:38])[C:35]([OH:39])=[C:34]([CH3:40])[CH:33]=2)[N:29]=[N:28][C:27]=1[O:41][CH3:42])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][OH:18])[CH:15]=2)[CH:10]=[C:9]1[C:26]1[CH:31]=[C:30]([C:32]2[CH:33]=[C:34]([CH3:40])[C:35]([OH:39])=[C:36]([CH3:38])[CH:37]=2)[N:29]=[N:28][C:27]=1[O:41][CH3:42])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 136383961HCID 136383961, compound

Product 1

HCID 136367317HCID 136367317, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.06 g 6-(tert-Butyldimethylsiloxymethyl)-2-[6-(4-hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-indole-1-carboxylic acid tert-butyl ester is dissolved in 50 mL THF. After addition of 4.1 g tetrabutylammonium fluoride trihydrate, the red solution is stirred for 2 hours. The reaction mixture is diluted with EtOAc, washed with saturated aqueous ammonium chloride, water, and brine, dried with MgSO4 and concentrated in vacuo. Purification on silica affords 2.04 g (82%) 6-hydroxymethyl-2-[6-(4-hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-indole-1-carboxylic acid tert-butyl ester.

Workup

  1. washwashed with saturated aqueous ammonium chloride, water, and brine
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification on silica

Sources & evidence

ORD record
ord-4e469a82c4e647fa95bb921cf5ce6dce
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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