N-bromobutanimide → 3-bromo-6-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 1622876Notes

Reaction equation

HRID 1622876 reaction equation
[F:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:11])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)Cl>[Br:12][C:10]1[C:5]2[C:6](=[N:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:8]([CH3:11])[CH:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 678165211H-Pyrrolo[2,3-b]pyridine, 6-fluoro-1-methyl-

Product 1

HCID 678140183-bromo-6-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridineYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridine (257.3 g, 1.71 mol) in DCM (3.86 L) is added N-bromosuccinimide (320.3 g; 1.80 mol) in five portions over 30 minutes. The mixture is stirred without heating or cooling overnight, then filtered and concentrated to about 1 L. This is purified by column chromatography on silica, eluting with 0 to 30% EtOAc in isohexane. The appropriate fractions are evaporated to give the product as an off white solid (391.3 g, 1.7 mol). 1H-NMR (400 MHz, CDCl3): δ 7.91-7.87 (m, 1H), 7.15 (s, 1H), 6.77 (d, 1H), 3.81 (s, 3H).

Workup

  1. temperaturewithout heating
  2. temperaturecooling overnight
  3. filtrationfiltered
  4. concentrationconcentrated to about 1 L
  5. customThis is purified by column chromatography on silica
  6. washeluting with 0 to 30% EtOAc in isohexane
  7. customThe appropriate fractions are evaporated

Sources & evidence

ORD record
ord-b3138332b814421a862db043f80dcc3a
Source dataset
uspto-grants-2014_07
Patent number
US08778946B2

Reaction notes

Loading…