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

HRID 911066Notes

Reaction equation

HRID 911066 reaction equation
[Br:1][C:2]1[C:3]([OH: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]([O: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 1785164645-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-ol

Product 1

HCID 866347803-(5-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-yloxy)-5-chloroisonicotinonitrileYield 7.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5-bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-ol (0.060 g, 0.16 mmol), 3,5-dichloroisonicotinonitrile (0.030 g, 0.18 mmol) and Cs2CO3 (0.057 g, 0.18 mmol) was stirred in DMSO (2 mL) at 100° C. overnight. The solution was cooled, quenched with water, extracted with EtOAc, dried, and concentrated. The crude material was purified by flash chromatography gave the desired product (0.006 g, 7% yield) as a white solid. 1H NMR (CDCl3) δ 8.55 (s, 1H), 8.50 (s, 1H), 8.27 (s, 1H), 7.12-7.26 (m, 5H), 6.87 (s, 1H), 6.37 (s, 1H), 2.89 (bs, 4H).

Workup

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

Sources & evidence

ORD record
ord-2a973e9399f741eba6784f809ddad006
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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