Sodium Azide → 4-Azido-5-bromo-2-(2,4-dichlorophenylamino)-3-fluorobenzoic acid methyl ester

HRID 500559Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([Br:10])[C:7](F)=[C:6]([F:12])[C:5]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21].[N-:23]=[N+:24]=[N-:25].[Na+]>CC(N(C)C)=O.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([N:23]=[N+:24]=[N-:25])=[C:6]([F:12])[C:5]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 5-bromo-2-(2,4-dichlorophenylamino)-3,4-difluorobenzoic acid methyl ester (2.02 g, 4.91 mmol) and NaN3 (379 mg, 5.83 mmol) in DMA (40 mL) was heated at 50° C. for 3 hours. The reaction mixture was diluted with EtOAc, and washed with water (5×). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to give the desired product (2.05 g, 96%) that was used directly without further purification.

Workup

washwashed with water (5×)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-729b0e0639f44a608a17f47dd449634d
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772234B2

Reaction notes

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