Bromine → 5-Bromo-3-(4-(trifluoromethyl)phenoxy)pyridin-2-amine
Reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[C:9]([NH2:14])=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:4]=1.[Br:19]Br>C(Cl)(Cl)Cl>[Br:19][C:12]1[CH:13]=[C:8]([O:7][C:6]2[CH:15]=[CH:16][C:3]([C:2]([F:1])([F:17])[F:18])=[CH:4][CH:5]=2)[C:9]([NH2:14])=[N:10][CH:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A 250 mL round-bottomed flask was charged with 3-(4-(trifluoromethyl)phenoxy)pyridin-2-amine (1.24 g, 4.88 mmol) and CHCl3 (150 mL), cooled to 0° C. and bromine (0.275 mL, 5.37 mmol) was added dropwise. The reaction was stirred for 60 minutes. The reaction was quenched into a saturated aqueous NaHCO3 solution and extracted with CH2Cl2 (2×150 mL). The combined organics were dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel eluting with 20% EtOAc/hexanes. The combined fractions of product were treated with charcoal, filtered through GFF paper and concentrated to afford the title compound (0.850 g, 52.3% yield) as a tan solid.
Workup
- customThe reaction was quenched into a saturated aqueous NaHCO3 solution
- extractionextracted with CH2Cl2 (2×150 mL)
- dry with materialThe combined organics were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified on silica gel eluting with 20% EtOAc/hexanes
- additionThe combined fractions of product were treated with charcoal
- filtrationfiltered through GFF paper
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-644794c99e164837af92b78221f4ce23
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08022223B2
Reaction notes
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