Cesium carbonate → 3-(5-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-ylthio)-5-chloroisonicotinonitrile

HRID 911059Notes

Reaction equation

HRID 911059 reaction equation
[Br:1][C:2]1[C:3]([SH:22])=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]=2)=[N:6][CH:7]=1.Cl[C:24]1[CH:31]=[N:30][CH:29]=[C:28]([Cl:32])[C:25]=1[C:26]#[N:27].C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[Br:1][C:2]1[C:3]([S:22][C:24]2[CH:31]=[N:30][CH:29]=[C:28]([Cl:32])[C:25]=2[C:26]#[N:27])=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:13]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 111375993,5-Dichloropyridine-4-carbonitrileHCID 1785277275-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridine-4-thiol

Product 1

HCID 866347743-(5-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-ylthio)-5-chloroisonicotinonitrileYield 49.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A flask was charged with 5-bromo-2-(4-phenethylthiazol-2-ylamino)pyridine-4-thiol (0.040 g, 0.10 mmol), 3,5-dichloroisonicotinonitrile (0.019 g, 0.11 mmol), Cs2CO3 (0.037 g, 0.11 mmol), and DMSO (2 mL). The reaction mixture was stirred at ambient temperature overnight, then quenched with water, extracted with EtOAc, dried, and concentrated. The crude material was purified by flash chromatography to provide the desired product (0.026 g, 48% yield) as a yellow solid. 1H NMR (CDCl3) δ 8.74 (d, 2H), 8.39 (s, 1H), 7.16-7.30 (m, 5H), 6.68 (s, 1H), 6.33 (s, 1H), 2.85-2.92 (m, 4H).

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. customdried
  4. concentrationconcentrated
  5. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-643023c9a1584667b838e04424a27ecd
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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