Ethyl Acetate → HCID 86634890, compound

HRID 420513Notes

Reaction equation

HRID 420513 reaction equation
Cl[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].[N-:21]=[N+:22]=[N-:23].[Na+].CCOC(C)=O>CN(C=O)C>[N:21]([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])=[N+:22]=[N-:23]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 66659136HCID 66659136, compound

Product 1

HCID 86634890HCID 86634890, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 8-chloro-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrile (80 mg, 0.25 mmol, prepared according to Example 23, Step 12.2) and sodium azide (81 mg, 1.24 mmol) in DMF (1 mL) was stirred and heated at 60° C. for 3 h. The reaction mixture was cooled to RT, poured into AcOEt and washed successively with water and brine. The organic layer was dried over Na2SO4, filtered and evaporated to yield the crude title compound (77.4 mg, 0.24 mmol, 95%) as a brownish solid, which was used in the next step without further purification. MS: 329 [M+1]+; HPLC: AtRet=2.56.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed successively with water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-995dddf139174b1eae9efae1ab2bdcdb
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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