2-Amino-5-bromopyridine → HCID 70427236, compound

HRID 542884Notes

Reaction equation

HRID 542884 reaction equation
[C:1]([C:9]([S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[CH:10]OCC)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][N:26]=1>CC(N(C)C)=O>[C:1]([C:9]([S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:15])=[O:16])=[CH:10][NH:24][C:25]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][N:26]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 543623313-Ethoxy-2-(4-methylbenzene-1-sulfonyl)-1-phenylprop-2-en-1-one

Product 1

HCID 70427236HCID 70427236, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 1-benzoyl-2-ethoxy-1-(4-methylphenylsulphonyl)ethene (0.85 g) and 2-amino-5-bromopyridine (0.45 g) in dimethylacetamide (30 ml) was heated at reflux for 2 hours. It was then cooled and poured onto ice (60 g). The resulting off-white precipitate was filtered off, washed with water, dried, and recrystallised from ethyl acetate, to give 1-benzoyl-2-(5-bromopyrid-2-ylamino)-1-(4-methylphenylsulphonyl)ethene (0.4 g), m.p. 205° C.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureIt was then cooled
  3. additionpoured onto ice (60 g)
  4. filtrationThe resulting off-white precipitate was filtered off
  5. washwashed with water
  6. customdried
  7. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-37f187f3d4354b6fb6d7eed3028ca29e
Source dataset
uspto-grants-1987_04
Patent number
US04659727

Reaction notes

Loading…