Sodium hydride → HCID 90409510, compound

HRID 1403728Notes

Reaction equation

HRID 1403728 reaction equation
[C:1]1([N:7]2[CH2:13][CH2:12][CH2:11][CH2:10][NH:9][S:8]2(=[O:15])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[C:21]([F:27])[CH:20]=1>CN(C=O)C.CCOC(C)=O.O>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[S:8]2(=[O:15])=[O:14])=[C:21]([F:27])[CH:20]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 27336604-Bromo-2-fluorobenzyl bromideHCID 90409894HCID 90409894, compound

Product 1

HCID 90409510HCID 90409510, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-phenyl-1λ6,2,7-thiadiazepane-1,1-dione (500 mg, 2.21 mmol) and NaH (214 mg, 6.63 mmol) in DMF (15 mL) was stirred at 0° C. for 10 minutes. To the solution was added a solution of 4-bromo-1-(bromomethyl)-2-fluorobenzene (881 mg, 3.32 mmol) in DMF (5 mL) and stirred at room temperature for 3 hours. The reaction mixture was diluted with EtOAc and water, extracted with ethyl acetate, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 2-[(4-bromo-2-fluorophenyl)methyl]-7-phenyl-1λ6,2,7-thiadiazepane-1,1-dione as a yellow oil (548 mg, 60%). LCMS (ESI): m/z=413.0 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-efc050c31453404d9656b36b8673cc22
Source dataset
uspto-grants-2014_12
Patent number
US08912219B2

Reaction notes

Loading…