Sodium hydride → HCID 11176842, compound

HRID 1945209Notes

Reaction equation

HRID 1945209 reaction equation
[H-].[Na+].[F:3][C:4]1[C:14]([F:15])=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[C:6]([OH:16])[CH:5]=1.[CH3:17][S:18]([C:21]1[CH:26]=[CH:25][C:24](F)=[C:23]([Cl:28])[CH:22]=1)(=[O:20])=[O:19]>CN(C=O)C>[Cl:28][C:23]1[CH:22]=[C:21]([S:18]([CH3:17])(=[O:20])=[O:19])[CH:26]=[CH:25][C:24]=1[O:16][C:6]1[CH:5]=[C:4]([F:3])[C:14]([F:15])=[CH:13][C:7]=1[O:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 213408802-Chloro-1-fluoro-4-methylsulfonylbenzeneHCID 66995735HCID 66995735, compound

Product 1

HCID 11176842HCID 11176842, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of sodium hydride (60% wt. disp. in oil, 0.275 g) and the product from step (iii) (0.7 g) in DMF (10 ml) was stirred at RT for 15 min. The product from example 7 step (ii) (0.715 g) was added and the mixture heated at 85° C. for 15 h. The mixture was partitioned between 2M sodium hydroxide solution and diethylether, the aqueous layer was acidified with 2M hydrochloric acid and extracted with ethylacetate. The ethylacetate layer was dried, evaporated under reduced pressure and the residue purified by RPHPLC. Yield 0.076 g.

Workup

  1. customThe mixture was partitioned between 2M sodium hydroxide solution and diethylether
  2. extractionextracted with ethylacetate
  3. dry with materialThe ethylacetate layer was dried
  4. customevaporated under reduced pressure
  5. customthe residue purified by RPHPLC

Sources & evidence

ORD record
ord-0522264dd1634cf1b08ca50f686d9435
Source dataset
uspto-grants-2013_03
Patent number
US08394986B2

Reaction notes

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