Hydrochloric Acid → HCID 15981403, compound

HRID 639712Notes

Reaction equation

HRID 639712 reaction equation
Cl.C(OC([N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]1[C:18]1[C:19](F)=[N:20][CH:21]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:23]=1)=O)(C)(C)C.[OH2:31]>O1CCOCC1>[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]1[C:18]1[C:19](=[O:31])[NH:20][CH:21]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 58917760HCID 58917760, compound

Product 1

HCID 15981403HCID 15981403, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Concentrated HCl (0.5 mL) was added dropwise to a stirred solution of 2-(2-fluoro-5-phenyl-pyridin-3-yl)-indole-1-carboxylic acid tert-butyl ester (113 mg, 0.29 mmol, 1.0 eq.) in dioxane (6 mL) and water (2 mL). The reaction was heated at reflux overnight. The reaction was cooled to ambient temperature and the solvent removed in vacuo. The crude residue was partitioned between water (10 mL) and EtOAc (15 mL) and the aqueous layer extracted with EtOAc (3×15 mL). The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by column chromatography on SiO2, eluting with 50% EtOAc/petroleum ether to 100% EtOAc to 10% MeOH/DCM to give the desired product as a yellow solid (25 mg, 0.09 mmol, 30%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. customthe solvent removed in vacuo
  4. customThe crude residue was partitioned between water (10 mL) and EtOAc (15 mL)
  5. extractionthe aqueous layer extracted with EtOAc (3×15 mL)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe residue was purified by column chromatography on SiO2
  10. washeluting with 50% EtOAc/petroleum ether to 100% EtOAc to 10% MeOH/DCM

Sources & evidence

ORD record
ord-3a4321615c07469982307d0d0bb8d18c
Source dataset
uspto-grants-2010_04
Patent number
US07691885B2

Reaction notes

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