Cesium carbonate → HCID 90031264, compound

HRID 624655Notes

Reaction equation

HRID 624655 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]1.Br[C:15]1[S:16][CH:17]=[CH:18][N:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.CN(C=O)C>[S:16]1[CH:17]=[CH:18][N:19]=[C:15]1[N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 764302-BromothiazoleHCID 589098Methyl indole-3-carboxylate

Product 1

HCID 90031264HCID 90031264, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of methyl 1H-indole-3-carboxylate (200 mg, 1.142 mmol) in NMP (Volume: 1142 μl) were added 2-bromothiazole (206 μl, 2.283 mmol) and cesium carbonate (1116 mg, 3.42 mmol) at RT. The mixture was heated at 110° C. for 2 h, then diluted with DMF, filtered and purified by HPLC to afford the title compound as a brown solid.

Workup

  1. filtrationfiltered
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-7dee03cd5d6a4cb8a509d3a3622a6b83
Source dataset
uspto-grants-2016_04
Patent number
US09303045B2

Reaction notes

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