HCID 66965464, compound → HCID 57948768, compound

HRID 555340Notes

Reaction equation

HRID 555340 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH3:21])[CH2:9][C:10]1[C:18]2[C:13](=[CH:14][C:15]([Cl:20])=[C:16]([F:19])[CH:17]=2)[NH:12][CH:11]=1)(C)(C)C>Cl.CO>[Cl:20][C:15]1[CH:14]=[C:13]2[C:18]([C:10]([CH2:9][C@@H:8]([NH2:7])[CH3:21])=[CH:11][NH:12]2)=[CH:17][C:16]=1[F:19]

Participants

3

Reactant 1

HCID 66965464HCID 66965464, compound

Product 1

HCID 57948768HCID 57948768, compound

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

A solution of [(S)-2-(6-chloro-5-fluoro-1H-indol-3-yl)-1-methyl-ethyl]-carbamic acid tert-butyl ester (200 mg, 0.6 mmol) in HCl/MeOH (10 mL) was stirred at room temperature. After TLC indicated the reaction was finished, the mixture was concentrated to remove the solvent. To the residue was added EtOAc (50 mL), and the mixture was neutralized with saturated NaHCO3 to pH 8˜9, and then extracted with EtOAc. The combined organic phases were dried with Na2SO4, filtered, concentrated to give a crude (S)-2-(6-chloro-5-fluoro-1H-indol-3-yl)-1-methyl-ethylamine which was used without further purification.

Workup

  1. concentrationthe mixture was concentrated
  2. customto remove the solvent
  3. additionTo the residue was added EtOAc (50 mL)
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic phases were dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-98fd233b09cc4a8582d6fa26408ac3e5
Source dataset
uspto-grants-2011_11
Patent number
US08053442B2

Reaction notes

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