Bromine → 4-(7-Bromo-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-1,2,5-oxadiazol-3-amine

HRID 1394188Notes

Reaction equation

[CH2:1]([N:3]1[C:11]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[N:5]=[C:4]1[C:12]1[C:13]([NH2:17])=[N:14][O:15][N:16]=1)[CH3:2].[Br:18]Br>C(O)(=O)C>[Br:18][C:10]1[C:11]2[N:3]([CH2:1][CH3:2])[C:4]([C:12]3[C:13]([NH2:17])=[N:14][O:15][N:16]=3)=[N:5][C:6]=2[CH:7]=[N:8][CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of the product of Example 1 Step 1 (3.0 g, 17.9 mmol) in acetic acid (40 ml) was added bromine (3.12 g, 1 ml, 19.7 mmol) and the mixture was heated at 100° C. for 20 hours. After cooling the solvent was removed in vacuo and the residue was partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic phase was washed with water (×3), dried and evaporated in vacuo. Purification of the residue by silica gel chromatography eluting with 50% dichloromethane in ethyl acetate afforded the title compound (1.9 g, 43%). 1H NMR (DMSO-d6) 8.73 (1H, s), 8.52 (1H, s), 7.0 (1H, br), 3.25 (2H, m), 1.16 (3H, t, J=7.2 Hz).

Workup

temperatureAfter cooling the solvent
customwas removed in vacuo
customthe residue was partitioned between dichloromethane and saturated sodium bicarbonate solution
washThe organic phase was washed with water (×3)
customdried
customevaporated in vacuo
customPurification of the residue by silica gel chromatography
washeluting with 50% dichloromethane in ethyl acetate

Sources & evidence

ORD record: ord-4c4e98340523408bb18625e72a0fd424
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348339B2

Reaction notes

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