N-bromobutanimide → HCID 66659003, compound

HRID 420536Notes

Reaction equation

HRID 420536 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

5

Reactant 2

HCID 67184N-bromobutanimideHCID 66659136HCID 66659136, compound

Product 1

HCID 66659003HCID 66659003, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

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.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-3ede47aa6c2b4b5c83d17583adadebf8
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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