TBAF tetrahydrofuran → HCID 22502794, compound

HRID 1814548Notes

Reaction equation

HRID 1814548 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:24]=[C:23]([F:25])[C:22]([O:26][CH2:27][CH2:28][O:29][Si](C(C)(C)C)(C)C)=[C:21]([F:37])[CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>O1CCCC1>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:24]=[C:23]([F:25])[C:22]([O:26][CH2:27][CH2:28][OH:29])=[C:21]([F:37])[CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 22503508HCID 22503508, compound

Product 1

HCID 22502794HCID 22502794, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The resulting 1-(4-ethylpiperazin-1-yl)-3-{3,5-difluoro-4-[2-(tert-butyldimethylsilyloxy)ethoxy]phenyl}isoquinoline (0.62 g) was dissolved in tetrahydrofuran (6 ml), to which was then added 1.0M tetrabutylammonium fluoride/tetrahydrofuran solution (1.41 ml), and the mixture was stirred for 75 min. The solvent was evaporated, and the resulting residue was dissolved in ethyl acetate, washed with (three times) and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol system), to give 0.46 g of the free compound of the title compound as a pale brown powder.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe resulting residue was dissolved in ethyl acetate
  3. washwashed with (three times) and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol system)

Sources & evidence

ORD record
ord-1a5835615ecf460aa6d245236b8d3c79
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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