Sodium Carbonate → HCID 88531037, compound

HRID 1916869Notes

Reaction equation

HRID 1916869 reaction equation
[CH2:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[C:6]2=[N:5][C:4]=1[NH:16][S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Br)=[CH:35][C:34]=1[C:41]([F:44])([F:43])[F:42]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([F:13])([F:14])[F:15])[C:6]2=[N:5][C:4]=1[N:16]([CH2:37][C:36]1[CH:39]=[CH:40][C:33]([F:32])=[C:34]([C:41]([F:44])([F:42])[F:43])[CH:35]=1)[S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:18])=[O:19])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27375774-Fluoro-3-(trifluoromethyl)benzyl bromideHCID 67954002HCID 67954002, compound

Product 1

HCID 88531037HCID 88531037, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 13-E (0.060 g, 0.1 mmol) in DMF (3 mL) was added Na2CO3 (0.032 g, 0.3 mmol) and 4-fluoro-3-trifluoromethylbenzyl bromide (0.028 g, 0.11 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 55 as a white solid (0.047 g, 87%); MS m/z (M+H+) 546.

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-9455bcde466549598d6280bc1d05abbe
Source dataset
uspto-grants-2013_12
Patent number
US08618150B2

Reaction notes

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