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

HRID 1486950Notes

Reaction equation

HRID 1486950 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[F:9][C:10]1[N:15]=[C:14]([NH2:16])[CH:13]=[CH:12][CH:11]=1>CC#N>[Br:8][C:11]1[CH:12]=[CH:13][C:14]([NH2:16])=[N:15][C:10]=1[F:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27613996-Fluoropyridin-2-amine

Product 1

HCID 534184365-Bromo-6-fluoropyridin-2-amineYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
15 °C

Procedure

NBS (50.0 g, 280.99 mmol) was added slowly to 6-fluoropyridin-2-amine (30 g, 267.61 mmol) in MeCN (300 mL) cooled to 10-20° C. over a period of 30 minutes. The resulting solution was stirred at ambient temperature for 60 minutes then the solvent removed under reduced pressure. The residue was diluted with water, the precipitate collected by filtration, washed with water (200 mL) and dried under vacuum to afford the desired material (50.0 g, 98%) as a white solid, which was used without further purification. NMR Spectrum: 1H NMR (300 MHz, DMSO-d6) δ 6.29 (1H, d), 6.57 (2H, bs), 7.65 (1H, t). Mass Spectrum: m/z (ES+)[M+H]+=191.

Workup

  1. customthe solvent removed under reduced pressure
  2. additionThe residue was diluted with water
  3. filtrationthe precipitate collected by filtration
  4. washwashed with water (200 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-6cbf6d159c9a4b61ae3bff8b3b1b584b
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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