Ammonia → (7-Bromoimidazo[1,2-A]pyridin-2-YL)methanamine

HRID 1487487Notes

Reaction equation

HRID 1487487 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([CH2:11]Cl)[N:10]=[C:4]2[CH:3]=1.[NH3:13]>CO>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([CH2:11][NH2:13])[N:10]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 441183127-Bromo-2-chloromethylimidazo[1,2-a]pyridine

Product 1

HCID 72209893(7-Bromoimidazo[1,2-A]pyridin-2-YL)methanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 7-Bromo-2-chloromethyl-imidazo[1,2-a]pyridine (0.325 g, 1.326 mmol) in methanol (5 mL), NH3 gas is purged at 0° C. for 30 minutes. The reaction is allowed to stir at room temperature for 16 hours. The solvent is concentrated to afford the title compound (0.315 g). 1H-NMR (400 MHz, DMSO-d6) δ: 4.15 (s, 2H), 7.12-7.15 (dd J1=1.96 Hz, J2=7.24 Hz, 1H), 7.90 (s, 1H), 8.03 (s, 1H), 8.32 (bs, 2H), 8.61 (d, J=7.2 Hz, 1H). LC-MS (m/z): [M+H]=225.9.

Workup

  1. concentrationThe solvent is concentrated

Sources & evidence

ORD record
ord-9fde02022379480d916c8b78eaa90ebd
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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