Hydrazine → 3-Bromo-5-fluoro-4-hydrazinylpyridine
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:9])[C:7]=1Cl.[NH2:10][NH2:11].C([O-])([O-])=O.[Na+].[Na+]>C1(O)CCCCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:9])[C:7]=1[NH:10][NH2:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-bromo-4-chloro-5-fluoro-pyridine (500 mg, 2.376 mmol), hydrazine (761.4 mg, 745.7 μL, 23.76 mmol), Na2CO3 (503.7 mg, 4.752 mmol) in cyclohexanol was heated at 100 C overnight. The reaction mixture was filtered on celite and loaded on a SCX column, washed with DCM/MeOH mixtures and was eluted with a 2M solution of NH3 in MeOH. The filtrate was concentrated in vacuo and the 3/1 mixture of 3-bromo-5-fluoro-4-hydrazinylpyridine and 3-bromo-4-chloro-5-hydrazinylpyridine was used in next step without further purification. MS (ES+) 205.9.
Workup
- filtrationThe reaction mixture was filtered on celite and
- washwashed with DCM/MeOH mixtures
- washwas eluted with a 2M solution of NH3 in MeOH
- concentrationThe filtrate was concentrated in vacuo
- additionthe 3/1 mixture of 3-bromo-5-fluoro-4-hydrazinylpyridine and 3-bromo-4-chloro-5-hydrazinylpyridine
- customwas used in next step without further purification
Sources & evidence
- ORD record
- ord-7547567c86c9499d93c7b3a0195ea27b
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340546B2
Reaction notes
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