Water → 2-Bromo-6-(difluoromethoxy)pyridin-3-amine

HRID 2042678Notes

Reaction equation

HRID 2042678 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]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 450909846-(Difluoromethoxy)pyridin-3-amine

Product 1

HCID 866522162-Bromo-6-(difluoromethoxy)pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic layer dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be65913758514361a2ac17f6149c502b
Source dataset
uspto-grants-2013_11
Patent number
US08586593B2

Reaction notes

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