Cesium carbonate → HCID 118060295, compound

HRID 2274810Notes

Reaction equation

HRID 2274810 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([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:32][CH2:33][N:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1>CN(C=O)C.[NH4+].[Cl-]>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:24]=[N:23][N:22]([CH2:32][CH2:33][N:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)[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

6

Reactant 3

HCID 10796Cesium carbonateHCID 816691-(2-Chloroethyl)pyrrolidineHCID 1180601346-fluoro-1-(phenylsulfonyl)-3-(1H-pyrazol-4-yl)-1H-indole2×

Product 1

HCID 118060295HCID 118060295, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 6-fluoro-1-(phenylsulfonyl)-3-(1H-pyrazol-4-yl)-1H-indole (Intermediate 5; 240 mg; 0.70 mmol) and Cs2CO3 (688 mg; 2.11 mmol) in DMF (20 mL) was added 1-(2-chloroethyl)-pyrrolidine (186 mg; 1.39 mmol). The reaction mixture was stirred at 65° C. for 2 hours, cooled to r.t., diluted with 10% aqueous NH4Cl (20 mL), and extracted with EtOAc (20 mL×3). The combined organic layers were washed with water (20 mL), brine (20 mL), dried over Na2SO4 anhydrous, and concentrated to afford 300 mg (98%) of the title compound as a yellow solid, which was used directly without further purification.

Workup

  1. temperaturecooled to r.t.
  2. extractionextracted with EtOAc (20 mL×3)
  3. washThe combined organic layers were washed with water (20 mL), brine (20 mL)
  4. dry with materialdried over Na2SO4 anhydrous
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-22afb2a720bb47feb1dc728f9d1c733d
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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