Pyridine → N-(5-bromopyridin-3-yl)-2-methylpropanamide

HRID 1397089Notes

Reaction equation

HRID 1397089 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.N1C=CC=CC=1.[C:15](Cl)(=[O:19])[CH:16]([CH3:18])[CH3:17]>C(Cl)Cl>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][C:15](=[O:19])[CH:16]([CH3:18])[CH3:17])[CH:3]=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62325Isobutyryl chlorideHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 68195778N-(5-bromopyridin-3-yl)-2-methylpropanamideYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-Amino-5-bromo pyridine (XXX)(leq) was dissolved in DCM and cooled to 0° C. before adding pyridine (2.2 eq) and isobutyryl chloride (XXXI) (1.1 eq). The reaction mixture was stirred at r.t. for 15 h until TLC showed the reaction was complete. The reaction mixture was diluted with DCM and washed with water. The organic extract was dried, concentrated and purified by column chromatography using silica gel (100-200 mesh) to afford N—(5-bromopyridin-3-yl)isobutyramide (XXXII) as a off white solid, (71% yield). 1H NMR (CDCl3) δ ppm 8.55-8.35 (m, 3H), 7.32 (s, 1H), 2.59-2.48 (m, 1H), 1.28-1.27 (d, 6H); ESIMS found C9H11BrN2O m/z 243.05 (M+H).

Workup

  1. washwashed with water
  2. extractionThe organic extract
  3. customwas dried
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-537968a23a7c48e4b63f54c5470aa9e1
Source dataset
uspto-grants-2014_12
Patent number
US08901150B2

Reaction notes

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