Tetrahydrofuran → HCID 58487036, compound
Reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][C:5]([NH2:8])=[CH:6][CH:7]=1.C(N(CC)CC)C.C1COCC1.[F:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>C(Cl)Cl>[NH2:9][C:3]1[N:4]=[C:5]([NH:8][C:25]([C:24]2[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=2[F:22])=[O:26])[CH:6]=[CH:7][C:2]=1[Br:1]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of 3-bromo-2,6-diaminopyridine (60) (564 mg, 3 mmol), triethyl amine (0.54 ml) in DCM (6 ml)/THF (4 ml) was cooled down to −78° C. A solution of 2-fluorobenzoyl chloride (362 μl, 3.03 mmol) in 2 ml DCM was added dropwise within 10 min. The resulting reaction mixture was stirred at −78° C. for 1 h before slowly warm up to r.t. After stirred at r.t. for 3 h, the reaction quenched with aq NaHCO3 solution. 200 ml EA were added. Org. phase was washed with brine, dried over sodium sulfate, concentrated. The light yellow solid residue was triturated with DCM (ca. 15 ml), filtered and dried to give 530 mg N-(6-amino-5-bromo(2-pyridyl))(2-fluorophenyl)carboxamide (61) as white solid. (purity>95%, yield: 57%).
Workup
- customThe resulting reaction mixture
- temperaturebefore slowly warm up to r.t
- stirringAfter stirred at r.t. for 3 h
- customthe reaction quenched with aq NaHCO3 solution
- addition200 ml EA were added
- washphase was washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe light yellow solid residue was triturated with DCM (ca. 15 ml)
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-cb35d74c5e89436dab67c8988ea6c2f5
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08980629B2
Reaction notes
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