Methanol → C-[6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methylamine

HRID 420493Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:18]#[N:19])=[CH:11][C:12]2[N:13]([CH:15]=[CH:16][N:17]=2)[CH:14]=1.B.C1COCC1.CO>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([CH2:18][NH2:19])=[CH:11][C:12]2[N:13]([CH:15]=[CH:16][N:17]=2)[CH:14]=1

Participants

Conditions

Temperature: 40 °C

Procedure

In a sealed flask, a solution of 6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrile (750 mg, 2.6 mmol) in THF (20 mL) was cautiously added to well stirred BH3.THF complex (1.0 M solution in THF, 13 mL, 13.0 mmol) at 0° C. The reaction mixture was heated at 40° C. for 1 h and cooled to RT. MeOH (large excess) and Amberlyst 15 (35 g) were successively added and the resulting mixture was shaken at RT for 30 min. The resin was filtered, washed with MeOH (500 mL), and the desired compound was released with ammonia (1.0 M solution in MeOH, 1.2 L). The NH3-MeOH fraction was evaporated to yield the crude C-[6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methylamine (778 mg) as a yellow oil.

Workup

temperaturecooled to RT
filtrationThe resin was filtered
washwashed with MeOH (500 mL)
customThe NH3-MeOH fraction was evaporated

Sources & evidence

ORD record: ord-503c9e429f1e49e5835cebdf280afe2b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097617B2

Reaction notes

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