N-bromobutanimide → 2-(4-Bromo-2-fluorophenylamino)-6-formylaminomethylnicotinic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH:12]=[O:13])=[N:6][C:5]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Si](C)(C)C)=[CH:17][C:16]=1[F:25].[Br:27]N1C(=O)CCC1=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH:12]=[O:13])=[N:6][C:5]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Br:27])=[CH:17][C:16]=1[F:25]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
To a solution of 2-(2-fluoro-4-trimethylsilanylphenylamino)-6-formylamino methyl-nicotinic acid methyl ester (11.6 g, 30.9 mmol) in DCM (300 mL) at −30° C. was added N-bromo succinimide (5.56 g, 30.9 mmol) portionwise. The reaction mixture was stirred at −30° C. for 30 minutes. The reaction mixture was concentrated in vacuo and the residue partitioned between saturated aqueous sodium hydrogen carbonate and ethyl acetate. The organic layer was separated and washed with water, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as an orange gum (11.8 g, 100%). LCMS (Method B): RT=3.67 min, M+H+=382/384.
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- customthe residue partitioned between saturated aqueous sodium hydrogen carbonate and ethyl acetate
- customThe organic layer was separated
- washwashed with water
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-0a1c3fd347084f609106a7f17d41b8fb
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206174B2
Reaction notes
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