Sodium Hydroxide → 5-(2-(((4-Bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinic acid

HRID 405170Notes

Reaction equation

HRID 405170 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[C:19]2[CH:20]=[CH:21][C:22]([C:25]([O:27]C)=[O:26])=[N:23][CH:24]=2)=[CH:6][C:5]=1[F:29]>C1COCC1>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[C:19]2[CH:20]=[CH:21][C:22]([C:25]([OH:27])=[O:26])=[N:23][CH:24]=2)=[CH:6][C:5]=1[F:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71060114Methyl 5-(2-(((4-bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinate

Product 1

HCID 710600525-(2-(((4-Bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 3M aqueous solution of NaOH (0.81 mL, 2.4 mmol) was added to a THF solution (13.7 mL) of methyl 5-(2-(((4-bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinate (350 mg, 0.8 mmol) and the resulting mixture was stirred at room temperature. After 2 h the resulting mixture was concentrated in vacuo, suspended in water, and acidified with 2 M HCl. The resulting precipitate was filtered off and dried in vacuo to yield the title compound.

Workup

  1. concentrationAfter 2 h the resulting mixture was concentrated in vacuo
  2. filtrationThe resulting precipitate was filtered off
  3. customdried in vacuo

Sources & evidence

ORD record
ord-a8fbce3775f3412ca1eaa475b866ed2b
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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