3-Fluorophenylhydrazine hydrochloride → [3-(6-Fluoro-2-methyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid

HRID 1466756Notes

Reaction equation

HRID 1466756 reaction equation
O=[C:2]([CH3:15])[CH2:3][S:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[CH:8]=[CH:9][CH:10]=1.Cl.[F:17][C:18]1[CH:19]=[C:20]([NH:24]N)[CH:21]=[CH:22][CH:23]=1>CC(O)(C)C>[F:17][C:18]1[CH:19]=[C:20]2[C:21]([C:3]([S:4][C:5]3[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[CH:8]=[CH:9][CH:10]=3)=[C:2]([CH3:15])[NH:24]2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 27239143-Fluorophenylhydrazine hydrochlorideHCID 66765032[3-(2-Oxo-propylsulfanyl)-phenyl]-acetic acid

Product 1

HCID 56840409[3-(6-Fluoro-2-methyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

[3-(2-Oxo-propylsulfanyl)-phenyl]-acetic acid (0.500 g, 2.2 mmol) and 3-fluorophenylhydrazine hydrochloride (0.400 g, 2.45 mmol) were dissolved in t-BuOH (10 mL). The reaction was stirred at 70° C. for 1.5 hours then submitted to aqueous workup. Purification by preparatory HPLC (10-100% ACN in H2O) afforded a 5:3 mixture of separable regioisomers of which the title compound was the major component.

Workup

  1. customPurification by preparatory HPLC (10-100% ACN in H2O)
  2. customafforded

Sources & evidence

ORD record
ord-fd068a57bf7d41268ec06b8d271ea71e
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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