Triethylamine → HCID 57516746, compound

HRID 1966579Notes

Reaction equation

HRID 1966579 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C(N(CC)CC)C.[Cl:16][CH2:17][C:18]([CH3:23])([CH3:22])[C:19](Cl)=[O:20]>ClCCl>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:19](=[O:20])[C:18]([CH3:23])([CH3:22])[CH2:17][Cl:16])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 706222-Amino-5-bromopyridine

Product 1

HCID 57516746HCID 57516746, compoundYield 116.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-5-bromopyridine (100 mg, 0.454 mmol) in dichloromethane (6 ml) were added triethylamine (0.19 ml, 1.364 mmol, 3 equiv.) and 3-chloro-2,2-dimethyl-propionyl chloride (CAS 4300-97-4) (140 mg, 0.909 mmol, 2 equiv.) at 0-5° C. The mixture was stirred for 16 hours at room temperature. The reaction mixture was evaporated and the crude product was purified by flash chromatography on silica gel column and eluting with an ethyl acetate:heptane gradient 5:95 to 10:90. The desired N-(5-bromo-pyridin-2-yl)-3-chloro-2,2-dimethyl-propionamide (154 mg, 74% yield) was obtained as a white solid.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe crude product was purified by flash chromatography on silica gel column
  3. washeluting with an ethyl acetate

Sources & evidence

ORD record
ord-bbb8bba167804ad786301d3c40e443dd
Source dataset
uspto-grants-2013_04
Patent number
US08420661B2

Reaction notes

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