Cesium carbonate → HCID 118060585, compound

HRID 2274801Notes

Reaction equation

HRID 2274801 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:21]=[N:22][NH:23][CH:24]=3)=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.[C:25]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:28])[CH:26]=[CH2:27].C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:24]=[N:23][N:22]([CH2:27][CH2:26][C:25]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:21]=3)=[CH:7][N:8]2[S:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 15458tert-Butyl acrylateHCID 1180601346-fluoro-1-(phenylsulfonyl)-3-(1H-pyrazol-4-yl)-1H-indole2×

Product 1

HCID 118060585HCID 118060585, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-fluoro-1-(phenylsulfonyl)-3-(1H-pyrazol-4-yl)-1H-indole (Intermediate 5; 100 mg; 0.29 mmol), tert-butyl acrylate (77 mg; 0.60 mmol) and Cs2CO3 (293 mg; 0.90 mmol) in MeCN (10 mL) was stirring at 80° C. overnight under nitrogen. The reaction mixture was filtered to remove solid and concentrated to afford 112 mg (82%) of the title compound as a yellow solid, which was used directly without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove solid
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-da005c6bafd74692b30421629ac26368
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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