N-bromobutanimide → (Rac)-3-[1-(3-bromo-imidazo[1,2-a]pyridin-6-yl)-ethyl]-6-(1-methyl-1h-pyrazol-4-yl)imidazo[1,2-b]pyridazine

HRID 69306Notes

Reaction equation

HRID 69306 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([CH:10]([C:12]3[N:16]4[N:17]=[C:18]([C:21]5[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=5)[CH:19]=[CH:20][C:15]4=[N:14][CH:13]=3)[CH3:11])[CH:7]=[CH:6][C:5]=12.C1C(=O)N([Br:34])C(=O)C1>C(Cl)Cl>[Br:34][C:3]1[N:4]2[CH:9]=[C:8]([CH:10]([C:12]3[N:16]4[N:17]=[C:18]([C:21]5[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=5)[CH:19]=[CH:20][C:15]4=[N:14][CH:13]=3)[CH3:11])[CH:7]=[CH:6][C:5]2=[N:1][CH:2]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57917425HCID 57917425, compound

Product 1

HCID 57917281(Rac)-3-[1-(3-bromo-imidazo[1,2-a]pyridin-6-yl)-ethyl]-6-(1-methyl-1h-pyrazol-4-yl)imidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(rac)-3-(1-Imidazo[1,2-a]pyridin-6-yl-ethyl)-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine (Example 293, 607 mg, 1.768 mmol) was dissolved in DCM (18 mL) and NBS (346 mg, 1.944 mmol) was added. It was stirred at rt for 30 min then the solvent was removed. The residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in DCM). Combined fractions were concentrated to give the title compound as a yellow solid (tR 0.7 min (conditions 2), MH+=422, 1H-NMR in DMSO-d6: 8.47 (s, 1H); 8.37 (s, 1H); 8.04 (m, 2H); 7.78 (s, 1H); 7.67 (s, 1H); 7.54 (d, 1H); 7.47 (d, 1H); 7.32 (d, 1H); 4.81 (q, 1H); 3.89 (s, 3H); 1.80 (d, 3H)).

Workup

  1. customthe solvent was removed
  2. customThe residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in DCM)
  3. concentrationCombined fractions were concentrated

Sources & evidence

ORD record
ord-35572baab7de40f989c3136453622910
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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