HCID 58188111, compound → Imidazo(1,2-a)pyridin-7-ylmethanamine

HRID 1845136Notes

Reaction equation

HRID 1845136 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[CH:12][N:13]=[C:7]2[CH:6]=1)=[N+]=[N-]>[Pd].C(OCC)(=O)C>[N:13]1[CH:12]=[CH:11][N:8]2[CH:9]=[CH:10][C:5]([CH2:4][NH2:1])=[CH:6][C:7]=12

Participants

4

Reactant 1

HCID 58188111HCID 58188111, compound

Product 1

HCID 55289825Imidazo(1,2-a)pyridin-7-ylmethanamineYield 93.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Into a round bottom flask were charged 7-(azidomethyl)imidazo[1,2-a]pyridine (1.5 g, 8.7 mmol), ethyl acetate (200 mL), and 10% Pd/C (250 mg). The mixture was stirred under hydrogen balloon at room temperature for 40 minutes. The mixture was filtered through Celite and the filtrate was concentrated to get the title product (1.2 g). 1H NMR (400 MHz, DMSO-d6): 8.48 (d, 1H, J=7.2 Hz), 7.88 (s, 1H), 7.52 (d, 1H, J=1.2 Hz), 7.51 (s, 1H), 6.89 (dd, 1H, J=7.2, 1.6 Hz), 3.83 (s, 2H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-35c2c18264844a4cb89325554c03f648
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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