Sodium Azide → Methyl 6-azido-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate

HRID 494700Notes

Reaction equation

HRID 494700 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7](=[O:25])[C:8]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[Cl:22])=[C:12]([Cl:23])[C:11](Cl)=[N:10][CH:9]=1>CN(C=O)C.O>[CH3:5][O:6][C:7](=[O:25])[C:8]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[Cl:22])=[C:12]([Cl:23])[C:11]([N:1]=[N+:2]=[N-:3])=[N:10][CH:9]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 11603943Methyl 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinate

Product 1

HCID 59519382Methyl 6-azido-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium azide (4.4 g, 68 mmol) was added to a suspension of 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinic acid methyl ester (26) (13.89 g, 33.8 mmol) in DMF (200 mL) and the mixture allowed to stir at room temperature overnight. The solution was diluted with water (600 mL) and the resulting white precipitate was collected by filtration and washed with water. The solids were dissolved into THF. Two volumes of diethyl ether were added and the organic solution washed with brine, dried over NaSO4, filtered, and concentrated in vacuo to the desired product (27) as a light yellow solid (12.94 g, 92%).

Workup

  1. filtrationthe resulting white precipitate was collected by filtration
  2. washwashed with water
  3. dissolutionThe solids were dissolved into THF
  4. additionTwo volumes of diethyl ether were added
  5. washthe organic solution washed with brine
  6. dry with materialdried over NaSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to the desired product (27) as a light yellow solid (12.94 g, 92%)

Sources & evidence

ORD record
ord-85f60a9474a742ee938e2975590010d8
Source dataset
uspto-grants-2009_05
Patent number
US07538120B2

Reaction notes

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