Tetrahydrofuran → 6-(2,6-Difluoro-4-(2-hydroxypropan-2-yl)phenyl)-5-fluoropicolinic acid

HRID 1499592Notes

Reaction equation

HRID 1499592 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([F:12])[C:3]=1[C:13]1[N:18]=[C:17]([C:19]([O:21]C)=[O:20])[CH:16]=[CH:15][C:14]=1[F:23].C1COCC1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([F:12])[C:3]=1[C:13]1[N:18]=[C:17]([C:19]([OH:21])=[O:20])[CH:16]=[CH:15][C:14]=1[F:23]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66655918Methyl 6-(2,6-difluoro-4-(2-hydroxypropan-2-yl)phenyl)-5-fluoropicolinate

Product 1

HCID 666524436-(2,6-Difluoro-4-(2-hydroxypropan-2-yl)phenyl)-5-fluoropicolinic acidYield 20.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The methyl 6-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-5-fluoropyridine-2-carboxylate prepared as described in Step 5 was treated with THF (8 mL), MeOH (8 mL) and 1.0 M aq. NaOH (8 mL, 8 mmol) at room temperature for 1 h. The volatile solvents were removed under reduced pressure. The residue was neutralized to pH around 6-7 with 1 M HCl. The precipitates were filtered, rinsed with water and dried to give the sub-title compound as a white solid (0.332 g, 20.8%). LCMS calc. for C15H13F3NO3 (M+H)+ m/z=312.1. found: 312.1.

Workup

  1. customThe volatile solvents were removed under reduced pressure
  2. filtrationThe precipitates were filtered
  3. washrinsed with water
  4. customdried

Sources & evidence

ORD record
ord-509c8bd519324d55b66a65cd94ae0c3d
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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