Sodium hydride → HCID 58772818, compound

HRID 2116531Notes

Reaction equation

HRID 2116531 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:29][C:30]([F:33])([F:32])[F:31]>C1COCC1>[F:31][C:30]([F:33])([F:32])[CH2:29][N:23]1[CH2:24][CH2:25][N:20]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:13]=2[N:12]=[CH:11][C:10]([S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:9])=[O:8])=[CH:19]3)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 678982-Bromo-1,1,1-trifluoroethaneHCID 11256720Intepirdine

Product 1

HCID 58772818HCID 58772818, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-phenylsulfonyl-8-piperazin-1-yl-quinoline (D12) (200 mg, 0.55 mmol) in dry THF (2 ml) was treated with sodium hydride (24 mg, 0.6 mmol, 60% oil dispersion), and 1-bromo-2,2,2-trifluoroethane (815 mg, 5 mmol). The mixture was heated to 100° C. for 4 days then cooled, evaporated and the residue subjected to purification by flash chromatography on silica gel (eluting with dichloromethane-methanol-aq. NH3) to give the free base form of the title compound. This was treated with 1M HCl in ether then crystallised from isopropanol to give the title compound (E8) as a yellow solid:

Workup

  1. temperaturethen cooled
  2. customevaporated
  3. customthe residue subjected to purification by flash chromatography on silica gel (eluting with dichloromethane-methanol-aq. NH3)

Sources & evidence

ORD record
ord-8ad9561595854b479f8cfe3a6fe59a9e
Source dataset
uspto-grants-2008_10
Patent number
US07439244B2

Reaction notes

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