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Thionyl Chloride → (E)-3-(3-hydroxy-4-methoxy-phenyl)-N-[1-(3-methyl-3H-imidazol-4-ylmethyl)-1H-indol-7-yl]-acrylamide

HRID 1184539
Notes
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Reaction equation

HRID 1184539 reaction equation
C([O:4][C:5]1[CH:6]=[C:7](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])(=O)C.O=S(Cl)Cl.[CH3:22][N:23]1[C:27]([CH2:28][N:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][C:36]=3[NH2:38])[CH:31]=[CH:30]2)=[CH:26][N:25]=[CH:24]1>C1COCC1>[OH:4][C:5]1[CH:6]=[C:7](/[CH:13]=[CH:14]/[C:15]([NH:38][C:36]2[CH:35]=[CH:34][CH:33]=[C:32]3[C:37]=2[N:29]([CH2:28][C:27]2[N:23]([CH3:22])[CH:24]=[N:25][CH:26]=2)[CH:30]=[CH:31]3)=[O:17])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 14214114(E)-3-(3-Acetoxy-4-methoxyphenyl)acrylic acidHCID 673378921-(3-methyl-3H-imidazol-4-ylmethyl)-1H-indol-7-ylamine

Product 1

HCID 67337739(E)-3-(3-hydroxy-4-methoxy-phenyl)-N-[1-(3-methyl-3H-imidazol-4-ylmethyl)-1H-indol-7-yl]-acrylamideYield 33.1%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

(E)-3-(3-Acetoxy-4-methoxyphenyl)acrylic acid (0.099 g, 0.420 mmol) was suspended in dry THF (8 ml). SOCl2 (0.037 ml, 0.504 mmol) was added and the mixture was stirred at RT for 1 h. The solvent was evaporated to dryness and the residue was dissolved in dry THF (8.00 ml). TEA (0.059 ml, 0.420 mmol) and 1-(3-methyl-3H-imidazol-4-ylmethyl)-1H-indol-7-ylamine (0.095 g, 0.420 mmol) were added. The mixture was stirred at RT for 18 hrs, heated at reflux for 5 hrs and then at RT for 48 hrs. The solvent was removed in vacuo and the residue was partitioned between EtOAc (10 ml) and H2O (2×10 ml). Organic phase was dried over sodium sulphate and concentrated to dryness. The crude was charged onto a SCX cartridge and eluted firstly with MeOH and then with NH3/MeOH. The title (E)-3-(3-hydroxy-4-methoxy-phenyl)-N-[1-(3-methyl-3H-imidazol-4-ylmethyl)-1H-indol-7-yl]-acrylamide (56 mg) was obtained after column chromatography (eluent: DCM 100% to DCM/MeOH 98:2).

Workup

  1. customThe solvent was evaporated to dryness
  2. dissolutionthe residue was dissolved in dry THF (8.00 ml)
  3. stirringThe mixture was stirred at RT for 18 hrs
  4. temperatureheated
  5. temperatureat reflux for 5 hrs
  6. waitat RT for 48 hrs
  7. customThe solvent was removed in vacuo
  8. customthe residue was partitioned between EtOAc (10 ml) and H2O (2×10 ml)
  9. dry with materialOrganic phase was dried over sodium sulphate
  10. concentrationconcentrated to dryness
  11. additionThe crude was charged onto a SCX cartridge
  12. washeluted firstly with MeOH

Sources & evidence

ORD record
ord-a0a195db1e7b4623ae0a7378ca62b5c0
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08669261B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes