2-Bromopropanal → 3-Methylimidazo[1,2-A]pyridine-6-carbonitrile

HRID 876830Notes

Reaction equation

HRID 876830 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.Br[CH:11]([CH3:14])[CH:12]=O>C(O)C>[CH3:14][C:11]1[N:3]2[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:2]2=[N:1][CH:12]=1

Participants

4

Reactant 2

HCID 3506242-BromopropanalHCID 8182602-Amino-5-cyanopyridine

Product 1

HCID 592142593-Methylimidazo[1,2-A]pyridine-6-carbonitrileYield 27.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-aminonicotinonitrile (1.2 g, 10.1 mmol) in ethanol (80 mL) was added 2-bromopropanal (6-1) (6.9 g, 50.5 mmol). The reaction mixture was stirred at 80° C. overnight. The solution was concentrated, diluted with water (20 mL) and adjusted to PH>7 with saturated aqueous NaHCO3 solution. The precipitate was collected to afford the title compound (430 mg). MS (m/z): 158 (M+H)+.

Workup

  1. concentrationThe solution was concentrated
  2. additiondiluted with water (20 mL)
  3. customThe precipitate was collected

Sources & evidence

ORD record
ord-672c9e708f94435293e82251533f7f98
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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