Cesium fluoride → HCID 67101807, compound

HRID 2079900Notes

Reaction equation

HRID 2079900 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:16]=3)[N:11]([CH:23]([CH3:25])[CH3:24])[CH:10]=2)[S:5][C:6]=1[C:7]#[N:8].[F-:26].[Cs+]>CS(C)=O.CCOC(C)=O>[C:7]([C:6]1[S:5][C:4]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:16]=3)[N:11]([CH:23]([CH3:25])[CH3:24])[CH:10]=2)=[CH:3][C:2]=1[F:26])#[N:8]

Participants

5

Reactant 2

HCID 25953Cesium fluorideHCID 24739673HCID 24739673, compound

Product 1

HCID 67101807HCID 67101807, compoundYield 3.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
21 °C

Procedure

Heat a mixture of N-[3-(4-Chloro-5-cyano-thiophen-2-yl)-1-isopropyl-1H-indol-6-yl]-methanesulfonamide (Example 118) (0.15 g, 0.381 mmol) and CsF (0.324 g, 2.13 mmol) in DMSO (5 ml) at 150° C. for 6 hours under N2. Cool the mixture to 21° C. and dilute with EtOAc. Wash the mixture with water, brine, and dried over MgSO4. Filter the material and concentrate to dryness. Purify the crude product by reverse phase chromatography to yield 5 mg of the title compound. MS: 378.0 (MH+)

Workup

  1. temperatureHeat
  2. washWash the mixture with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationFilter the material
  5. concentrationconcentrate to dryness
  6. customPurify the crude product by reverse phase chromatography

Sources & evidence

ORD record
ord-6d22f07546504aa7b0a894328dec63f8
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Reaction notes

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