4-(4-Ethylpiperazin-1-yl)-6-(4-methoxyphenyl)thieno[3,2-c]pyridine → 4-(4-Ethylpiperazin-1-yl)-6-(4-hydroxyphenyl)thieno[3,2-c]pyridine

HRID 1006951Notes

Reaction equation

HRID 1006951 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]C)=[CH:20][CH:19]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2]>Br>[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]([OH:24])=[CH:20][CH:19]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

3

Reactant 1

HCID 225028824-(4-Ethylpiperazin-1-yl)-6-(4-methoxyphenyl)thieno[3,2-c]pyridine

Product 1

HCID 1357190444-(4-Ethylpiperazin-1-yl)-6-(4-hydroxyphenyl)thieno[3,2-c]pyridineYield 80.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

4-(4-Ethylpiperazin-1-yl)-6-(4-methoxyphenyl)thieno[3,2-c]pyridine (5.2 g) was dissolved in 48% hydrobromic acid (50 ml), and the mixture was reacted at 130° C. for 1.5 hr. The reaction solution was evaporated, basified with potassium carbonate and extracted with chloroform. The chloroform layer was washed with water, dried and evaporated. The resulting residue was purified by NH-silica gel column chromatography (ethyl acetate), to give the title compound as a pale brown powder (4.0 g, yield; 80%).

Workup

  1. customthe mixture was reacted at 130° C. for 1.5 hr
  2. customThe reaction solution was evaporated
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed with water
  5. customdried
  6. customevaporated
  7. customThe resulting residue was purified by NH-silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-d8e26866ae294449991c25d4844ee7f5
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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