Acetic Acid → 5-bromo-N-(pyrimidin-4-yl)naphthalene-2-sulfonamide
Reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([O:15]C1C(F)=C(F)C(F)=C(F)C=1F)(=[O:14])=O)=[CH:7]2.[N:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[N:29][CH:28]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C(O)(=O)C>>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([NH:33][C:30]1[CH:31]=[CH:32][N:27]=[CH:28][N:29]=1)(=[O:14])=[O:15])=[CH:7]2Participants
Conditions
- Temperature
- -78 °C
Procedure
A round bottom flask was charged with perfluorophenyl 5-bromonaphthalene-2-sulfonate (Intermediate M) (0.677 g, 1.494 mmol) and pyrimidin-4-amine (0.185 g, 1.942 mmol). A septum was attached and the flask flushed with N2. THF (7.47 mL) was added and the solution was cooled to −78° C., lithium bis(trimethylsilyl)amide (1.195 mL, 1.195 mmol) was added and after addition was complete, the cold bath was removed and the solution was allowed to warm to rt. After 30 min at rt, acetic acid (0.257 mL, 4.48 mmol) was added to the solution to produce a precipitate. The mixture was concentrated and the resulting tan solid was suspended in DCM (20 mL) and collected by vacuum filtration to provide 5-bromo-N-(pyrimidin-4-yl)naphthalene-2-sulfonamide (0.54 g) as a tan solid, which was of sufficient purity for further use.
Workup
- customthe flask flushed with N2
- additionTHF (7.47 mL) was added
- additionafter addition
- customthe cold bath was removed
- temperatureto warm to rt
- customto produce a precipitate
- concentrationThe mixture was concentrated
- filtrationcollected by vacuum filtration
Sources & evidence
- ORD record
- ord-857575946cfa4c7baed558aeaadacfe7
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012443B2
Reaction notes
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