N-bromobutanimide → 5-Bromo-6-fluoropyridin-2-amine

HRID 501056Notes

Reaction equation

HRID 501056 reaction equation
[F:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[Br:9]N1C(=O)CCC1=O>C(#N)C>[Br:9][C:3]1[CH:4]=[CH:5][C:6]([NH2:8])=[N:7][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 27613996-Fluoropyridin-2-amine

Product 1

HCID 534184365-Bromo-6-fluoropyridin-2-amineYield 170.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 6-fluoro-pyridin-2-ylamin (1.0 g, 8.93 mmol) in acetonitrile (50 mL), protected from light and under nitrogen atmosphere, N-bromosuccinimide (0.79 g, 4.46 mmol) was added. After 1 hour, an additional portion of N-bromosuccinimide (0.79 g, 4.46 mmol) was added and the stirring was continued for 3 hours. The volatiles were removed under reduced pressure and the crude material was purified by flash column chromatography using a gradient of 25% to 30% ethyl acetate in hexane to give 5-bromo-6-fluoro-pyridin-2-ylamine (1.45 g) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ: 7.60 (t, J=8.59 Hz, 1 H) 6.15-6.36 (m, 1 H) 4.58 (br. s., 2 H)

Workup

  1. waitthe stirring was continued for 3 hours
  2. customThe volatiles were removed under reduced pressure
  3. customthe crude material was purified by flash column chromatography

Sources & evidence

ORD record
ord-2ec203d5a954441da50f5f985c7c30f9
Source dataset
uspto-grants-2010_08
Patent number
US07772256B2

Reaction notes

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