Sodium Carbonate → HCID 67954032, compound

HRID 2178577Notes

Reaction equation

HRID 2178577 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-d60bbfada054480d82d30e19d9b0ae29
Source dataset
uspto-grants-2015_06
Patent number
US09067935B2

Reaction notes

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