Cesium carbonate → 6-(6-Bromo-pyridin-3-yl)-4H-1-thia-4,5-diaza-cyclopenta[a]pentalen-7-one

HRID 532637Notes

Reaction equation

HRID 532637 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:12]3[CH2:13][C:14]4[S:15][CH:16]=[CH:17][C:18]=4[C:11]=3[NH:10][N:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=[O:20].[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:12]3[C:13](=[O:20])[C:14]4[S:15][CH:16]=[CH:17][C:18]=4[C:11]=3[NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 718150976-(6-Bromo-pyridin-3-yl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene

Product 1

HCID 718151666-(6-Bromo-pyridin-3-yl)-4H-1-thia-4,5-diaza-cyclopenta[a]pentalen-7-oneYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-(6-Bromo-pyridin-3-yl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.32 g, 1.0 mmol) and Cs2CO3 (3.26 g, 10.0 mmol) in DMF (10 mL) was stirred under molecular oxygen at ambient temperature. The reaction mixture was stirred for 12 hr. Afterward, the mixture was poured into ice water, followed by aqueous wash and evaporation of the solvent, which provided the corresponding 6-(6-Bromo-pyridin-3-yl)-4H-1-thia-4,5-diaza-cyclopenta[a]pentalen-7-one (0.31 g, 0.92 mmol) as orange solid in 92% yield.

Workup

  1. stirringThe reaction mixture was stirred for 12 hr
  2. washby aqueous wash
  3. customevaporation of the solvent, which

Sources & evidence

ORD record
ord-a8bea751a79743f79b6085e734946916
Source dataset
uspto-grants-2014_10
Patent number
US08853207B2

Reaction notes

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