2-Amino-5-bromopyridine → HCID 88658071, compound

HRID 1905646Notes

Reaction equation

HRID 1905646 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[CH:12]OCC)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][N:27]=1>CC(N(C)C)=O>[Br:32][C:29]1[CH:30]=[CH:31][C:26]([NH:25][CH:12]=[C:11]([S:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)(=[O:10])=[O:9])[S:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)(=[O:17])=[O:18])=[N:27][CH:28]=1

Participants

4

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 53835479HCID 53835479, compound

Product 1

HCID 88658071HCID 88658071, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 1-(3-chlorophenylsulphonyl)-2-ethoxy-1-phenylsulphonylethene (3.13 g) and 2-amino-5-bromopyridine (1.4 g) in dimethylacetamide (20 ml) was heated at reflux for 3.5 hours. The solution was cooled and poured onto ice (200 g), and the resulting pale yellow solid was filtered off and recrystallised from aqueous ehtaol (95% v/v), to give 2-(5-bromopyrid-2-ylamino)-1-(3-chloropheylsulphonyl)-1-phenylsulphonylethene (2.5 g), m.p. 170°-172° C.

Workup

  1. temperatureat reflux for 3.5 hours
  2. temperatureThe solution was cooled
  3. additionpoured onto ice (200 g)
  4. filtrationthe resulting pale yellow solid was filtered off
  5. customrecrystallised from aqueous ehtaol (95% v/v),

Sources & evidence

ORD record
ord-4b501b4434b94867a99371ec7109d024
Source dataset
uspto-grants-1987_03
Patent number
US04647569

Reaction notes

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