Sodium Carbonate → HCID 88531023, compound

HRID 1916862Notes

Reaction equation

HRID 1916862 reaction equation
[CH3:1][C:2]1[N:6]2[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17].C([O-])([O-])=O.[Na+].[Na+].[F:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[C:40]([F:43])([F:42])[F:41])[CH2:35]Br>CN(C=O)C.C(OCC)(=O)C>[F:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[C:40]([F:41])([F:42])[F:43])[CH2:35][N:15]([C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:7][N:6]2[C:2]=1[CH3:1])[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27375744-(Bromomethyl)-2-fluoro-1-(trifluoromethyl)benzeneHCID 67953983HCID 67953983, compound

Product 1

HCID 88531023HCID 88531023, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 10-G (0.023 g, 0.048 mmol) in DMF (1 mL) was added Na2CO3 (0.015 g, 0.14 mmol) and 3-fluoro-4-trifluoromethylbenzyl bromide (0.014 g, 0.053 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 100 as a yellow solid (0.017 g, 66%); MS m/z (M+H+) 532.

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-55cdc4b8b0004a49bf88540e801e2a81
Source dataset
uspto-grants-2013_12
Patent number
US08618150B2

Reaction notes

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