N-bromobutanimide → HCID 66659003, compound

Reaction equation

[Cl:1][C:2]1[C:3]2[N:4]([CH:18]=[CH:19][N:20]=2)[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:7]=1[C:8]#[N:9].C1C(=O)N([Br:28])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Br:28][C:18]1[N:4]2[CH:5]=[C:6]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])[C:7]([C:8]#[N:9])=[C:2]([Cl:1])[C:3]2=[N:20][CH:19]=1

Participants

Procedure

A solution of 8-chloro-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrile (1.5 g, 4.65 mmol, prepared according to Example 23, Step 12.2) in DMF (19 mL) was treated with NBS (910 mg, 5.12 mmol) at RT and stirred for 1 h. The reaction mixture was diluted in AcOEt and washed with water. The organic layer was dried over Na2SO4, filtered and evaporated to yield the crude title compound (1.92 g, 4.65 mmol, quant.), which was used in the next step without further purification. MS: 400 [M+1]+; HPLC: AtRet=2.67.