Water → 2-Bromo-6-(difluoromethoxy)pyridin-3-amine
Reaction equation
[F:1][CH:2]([F:11])[O:3][C:4]1[N:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.[Br:12]N1C(=O)CCC1=O.O>C(#N)C>[Br:12][C:8]1[C:7]([NH2:10])=[CH:6][CH:5]=[C:4]([O:3][CH:2]([F:1])[F:11])[N:9]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
6-Difluoromethoxy-pyridin-3-yl-amine obtained in Step B (1.36 g) was treated with N-bromosuccinimide (1.51 g) in acetonitrile for 10 minutes. The solution was poured into water, extracted with ethyl acetate, the organic layer dried over sodium sulfate and concentrated in vacuo. Chromatography on silica gel (eluent: cyclohexane/ethyl acetate 7:3) afforded 2-bromo-6-difluoromethoxy-pyridin-3-yl-amine as a red oil. 1H NMR (400 MHz, CDCl3) 3.95 (br s, 2H), 6.72 (d, 1H), 7.07 (d, 1H), 7.24 (dd, 1H).
Workup
- extractionextracted with ethyl acetate
- dry with materialthe organic layer dried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-be65913758514361a2ac17f6149c502b
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586593B2
Reaction notes
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