5-Bromo-6-chloropyridine-3-carboxylic acid → HCID 86665190, compound

HRID 2179448Notes

Reaction equation

HRID 2179448 reaction equation
[Br:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]>O1CCCC1.CN(C)C1C=CN=CC=1.O.Cl>[Br:1][C:2]1[CH:10]=[C:6]([C:7]([O:9][C:6]([CH3:10])([CH3:7])[CH3:5])=[O:8])[CH:5]=[N:4][C:3]=1[Cl:11]

Participants

6

Reactant 1

HCID 2854335-Bromo-6-chloropyridine-3-carboxylic acid

Product 1

HCID 86665190HCID 86665190, compoundYield 154.8%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-6-chloronicotinic acid (25.0 g, 106 mmol) in tetrahydrofuran (1.06 L) was added di-tort-butyl dicarbonate (69.2 g, 317 mmol) followed by 4-dimethylaminopyridine (12.9 g, 106 mmol). After 16 h, the mixture was diluted with water and aqueous hydrochloric acid was added (106 mL, 1 M, 106 mmol). The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine (3×), dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→10% methanol/dichloromethane) gave the title compound (24.0 g). MS 292.96 (M).

Workup

  1. additionwas added (106 mL, 1 M, 106 mmol)
  2. extractionThe mixture was extracted with ethyl acetate (3×)
  3. washThe combined organic extracts were washed with brine (3×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (100% dichloromethane→10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-68fbec5403a64736abcfef8765f8d132
Source dataset
uspto-grants-2015_06
Patent number
US09067941B2

Reaction notes

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