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

HRID 217279Notes

Reaction equation

HRID 217279 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, Hz, 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-0dd6da55e05c4292b7711f681e3c8c89
Source dataset
uspto-grants-2012_06
Patent number
US08193362B2

Reaction notes

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