Hydrochloric Acid → 2-(5-bromopyridin-3-yl)-1H-indole

HRID 712604Notes

Reaction equation

HRID 712604 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[CH:18]=[N:19][CH:20]=[C:21]([Br:23])[CH:22]=1)=O)(C)(C)C.Cl>CCOC(C)=O>[Br:23][C:21]1[CH:22]=[C:17]([C:9]2[NH:8][C:16]3[C:11]([CH:10]=2)=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:18]=[N:19][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1176674442-(5-Bromo-pyridin-3-yl)-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 582156752-(5-bromopyridin-3-yl)-1H-indoleYield 81.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(5-Bromo-pyridin-3-yl)-indole-1-carboxylic acid tert-butyl ester (320 mg, 0.86 mmol) is added into 4.0 M HCl in EtOAc (10 mL) and the solution is stirred at room temperature for 16 hrs. The solvent is evaporated and the residue is dissolved in water and saturated aqueous NaHCO3 solution is used to adjusted the pH to 9-10. Then the mixture is extracted with DCM for three times. The organic layers are combined, dried over Na2SO4, filtered and concentrated to give 192 mg of the crude 2-(5-bromo-pyridin-3-yl)-1H-indole which is used in the next step directly.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue is dissolved in water
  3. extractionThen the mixture is extracted with DCM for three times
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-93d8f4402b7f49a398ce3eb8a4f7d2ca
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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