Sodium Carbonate → HCID 67954032, compound

HRID 1916874Notes

Reaction equation

HRID 1916874 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:26])=[C:9]([NH:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:25]=[CH:24][CH:23]=[N:22]4)=[CH:17][CH:16]=3)(=[O:14])=[O:13])[N:10]=2)[CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[F:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Br)=[CH:36][C:35]=1[C:42]([F:45])([F:44])[F:43]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:26])=[C:9]([N:11]([CH2:38][C:37]3[CH:40]=[CH:41][C:34]([F:33])=[C:35]([C:42]([F:45])([F:43])[F:44])[CH:36]=3)[S:12]([C:15]3[CH:16]=[CH:17][C:18]([N:21]4[CH:25]=[CH:24][CH:23]=[N:22]4)=[CH:19][CH:20]=3)(=[O:14])=[O:13])[N:10]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27375774-Fluoro-3-(trifluoromethyl)benzyl bromideHCID 67953954HCID 67953954, compound

Product 1

HCID 67954032HCID 67954032, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 16-C (0.011 g, 0.27 mmol) in DMF (0.5 mL) was added Na2CO3 (0.0057 g, 0.054 mmol) and 4-fluoro-3-trifluoromethylbenzyl bromide (0.0077 g, 0.03 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with water, and dried over sodium sulfate. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography, eluting with a hexanes-EtOAc gradient to give Compound 102 (0.011 g, 72%) as a white solid; MS m/z (M+H+) 564.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by flash column chromatography
  5. washeluting with a hexanes-EtOAc gradient

Sources & evidence

ORD record
ord-20e79b8965d5493eac95562a92205cac
Source dataset
uspto-grants-2013_12
Patent number
US08618150B2

Reaction notes

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