Hydrochloric Acid → 4-(2-Amino-5-bromopyridin-3-yl)-2-fluorobenzoic acid

HRID 595941Notes

Reaction equation

HRID 595941 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:6][C:5]([Br:19])=[CH:4][N:3]=1.[Li+].[OH-].Cl.CCOC(C)=O>C1COCC1.CO>[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:6][C:5]([Br:19])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 118045477Methyl 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoate

Product 1

HCID 1180467884-(2-Amino-5-bromopyridin-3-yl)-2-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoate (1.9 g, 5.84 mmol) in THF (19.48 mL) and MeOH (9.74 mL, Ratio: 1.000) was added LiOH (1 M aqueous solutionueous solution) (10.52 mL, 10.52 mmol). The reaction mixture was stirred for 5 h. After 1N HCl (1.9 mL) was added up to pH 5, the reaction mixture was worked up with EtOAc, the organic layer was dried over Na2SO4, filtered off and concentrated in vacuo. The crude 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoic acid was used for the next step without further purification. LCMS (m/z): 311.1/313.1 (MH+), 0.5 min.

Workup

  1. dry with materialthe organic layer was dried over Na2SO4
  2. filtrationfiltered off
  3. concentrationconcentrated in vacuo
  4. customThe crude 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoic acid was used for the next step without further purification
  5. custom311.1/313.1 (MH+), 0.5 min.

Sources & evidence

ORD record
ord-fa4c0f59979c4c3fbde172247a9d4431
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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