TBAF tetrahydrofuran → 4-(4-Ethylpiperazin-1-yl)-6-[4-(2-hydroxypropoxy)phenyl]thieno[3,2-c]pyridine

HRID 1251182Notes

Reaction equation

HRID 1251182 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:14]3[CH:15]=[CH:16][S:17][C:13]=3[CH:12]=[C:11]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([O:28][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[CH3:27])=[CH:20][CH:19]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>C1COCC1>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:14]3[CH:15]=[CH:16][S:17][C:13]=3[CH:12]=[C:11]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([OH:28])[CH3:27])=[CH:20][CH:19]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 207703824-(4-Ethylpiperazin-1-yl)-6-[4-(2-t-butyldiphenylsilyloxypropoxy)phenyl]thieno[3,2-c]pyridine

Product 1

HCID 99088034-(4-Ethylpiperazin-1-yl)-6-[4-(2-hydroxypropoxy)phenyl]thieno[3,2-c]pyridineYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Ethylpiperazin-1-yl)-6-[4-(2-t-butyldiphenylsilyloxypropoxy)phenyl]thieno[3,2-c]pyridine of 3.38 g (5.31 mmol) was dissolved in THF of 20 ml and stirred at room temperature. To the mixture was added 1.0M tetrabutylammonium fluoride/THF solution of 10.6 ml (2.0 equivalents), and the mixture was stirred for 8 hr. The solvent was evaporated, and to the resulting residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with water (three times) and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by NH-silica gel column chromatography (n-hexane/ethyl acetate system), to give the title compound as a colorless oil (1.65 g, yield; 78%).

Workup

  1. stirringthe mixture was stirred for 8 hr
  2. customThe solvent was evaporated
  3. additionto the resulting residue was added water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed sequentially with water (three times) and brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting residue was purified by NH-silica gel column chromatography (n-hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-66254ed6cc3e4746b945cb4945880e3f
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

Loading…