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

HRID 1814500Notes

Reaction equation

HRID 1814500 reaction equation
[H-].[Na+].[CH2:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:16]3[CH:17]=[CH:18][S:19][C:15]=3[CH:14]=[C:13]([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)[N:12]=2)[CH2:7][CH2:6]1)[CH3:4].Br[CH:28]([SiH](C1C=CC=CC=1)C1C=CC=CC=1)[CH:29]([O:31]C(C)(C)C)[CH3:30].O>CCCCCC.CN(C=O)C>[CH2:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:16]3[CH:17]=[CH:18][S:19][C:15]=3[CH:14]=[C:13]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:28][CH:29]([OH:31])[CH3:30])=[CH:22][CH:21]=3)[N:12]=2)[CH2:7][CH2:6]1)[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1317248261-bromo-O-(t-butyl)diphenylsilyl-2-propanolHCID 1357190444-(4-Ethylpiperazin-1-yl)-6-(4-hydroxyphenyl)thieno[3,2-c]pyridine

Product 1

HCID 99088034-(4-Ethylpiperazin-1-yl)-6-[4-(2-hydroxypropoxy)phenyl]thieno[3,2-c]pyridineYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8058HexaneSolvent

Procedure

66% sodium hydride (0.26 g, 1.2 equivalents) was washed with n-hexane and was then suspended in DMF of 1 ml, and the mixture was stirred under ice-cooling. To the resulting mixture was added 4-(4-ethylpiperazin-1-yl)-6-(4-hydroxyphenyl)thieno[3,2-c]pyridine of 2.00 g (5.88 mmol) dissolved in DMF of 20 ml, followed by the agitation at room temperature for 45 min. To the resulting product was added 1-bromo-O-(t-butyl)diphenylsilyl-2-propanol of 4.44 g (2.0 equivalents) dissolved in DMF of 15 ml, which was stirred in nitrogen atmosphere at 50° C. for 18 hr. Water was added to the resulting mixture, and then 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 (eluent solvent/ethyl acetate system), to give the title compound as a pale yellow oil (3.38 mg, yield; 90%).

Workup

  1. temperaturecooling
  2. stirringwas stirred in nitrogen atmosphere at 50° C. for 18 hr
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed sequentially with water (three times) and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe resulting residue was purified by NH-silica gel column chromatography (eluent solvent/ethyl acetate system)

Sources & evidence

ORD record
ord-4c9b6b0605cc4ee49537cea10d01e744
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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