Pivaloyl chloride → HCID 89619215, compound

HRID 1502120Notes

Reaction equation

HRID 1502120 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:9])[CH:3]=1.CCN(C(C)C)C(C)C.[C:19](Cl)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21]>C(Cl)Cl.[Cl-].[Na+].O>[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:4]([CH3:9])[CH:3]=1

Participants

6

Reactant 3

HCID 62493Pivaloyl chloride2×HCID 81531DiisopropylethylamineHCID 199260946-Bromo-4-methylpyridin-3-amine

Product 1

HCID 89619215HCID 89619215, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

6-Bromo-4 methyl-3 pyridinamine (1.03 g, 5.51 mmol) was dissolved in DCM (20 ml) at 0° C. then added Hunig's Base (1.154 ml, 6.61 mmol) followed by pivaloyl chloride (0.745 ml, 6.06 mmol). After stirring for 1 hr, the reaction was not complete. Another equivalent of TEA and pivaloyl chloride were added then stirred for an hour. The reaction was poured into brine and extracted with DCM (2×). The organic layer was separated and dried over Na2SO4, filtered and concentrated. The residue was chromatographed thru a 200 g ISCO redisep column and eluted with 5% MeOH/DCM to yield title compound. LC-MS: M+2=273;

Workup

  1. stirringthen stirred for an hour
  2. extractionextracted with DCM (2×)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed thru a 200 g ISCO redisep column
  8. washeluted with 5% MeOH/DCM

Sources & evidence

ORD record
ord-f1216c746dd947e3bb1fffb492c12033
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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