Dimethylformamide → 6-(2-bromo-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

HRID 469311

Reaction equation

S(Cl)(Cl)=O.CN(C=O)C.[Br:10][C:11]1[CH:16]=[C:15]([C:17]([OH:19])=O)[CH:14]=[CH:13][N:12]=1.[Cl-].[Cl-].[Cl-].[Al+3].[CH3:24][C:25]1[C:30]2[NH:31][C:32](=[O:34])[O:33][C:29]=2[CH:28]=[CH:27][CH:26]=1.BrBr.ClCl>C(Cl)Cl>[Br:10][C:11]1[CH:16]=[C:15]([C:17]([C:27]2[CH:26]=[C:25]([CH3:24])[C:30]3[NH:31][C:32](=[O:34])[O:33][C:29]=3[CH:28]=2)=[O:19])[CH:14]=[CH:13][N:12]=1

Participants

Conditions

Temperature: 130 °C

Procedure

2.20 mL (30.0 mmol) thionyl chloride and 0.390 mL (4.80 mmol) DMF were added to 2.00 g (9.90 mmol) 2-bromopyridine-4-carboxylic acid in 30 mL DCM and refluxed for 2 h. The reaction mixture was evaporated to dryness and coevaporated twice with toluene. The residue was combined with 6.24 g (46.8 mmol) aluminium trichloride and 1.50 g (10.1 mmol) 4-methyl-3H-benzoxazol-2-one and the mixture obtained was stirred overnight at 110° C. and for 5 hours at 130° C. The mixture was decomposed with ice water and extracted twice with DCM. The organic phases were dried on magnesium sulphate, filtered and evaporated down i. vac. The residue was triturated with DIPE/MeOH and suction filtered. The product obtained is a mixture of the corresponding bromine and chlorine compound (40/60).

Workup

temperaturerefluxed for 2 h
customThe reaction mixture was evaporated to dryness
customthe mixture obtained
extractionextracted twice with DCM
customThe organic phases were dried on magnesium sulphate
filtrationfiltered
customevaporated down i
customThe residue was triturated with DIPE/MeOH and suction
filtrationfiltered
customThe product obtained

Sources & evidence

ORD record: ord-a7869bb0c12f4d85aef225774e98f332
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629137B2

Linked notes

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