Potassium Carbonate → HCID 22648134, compound

HRID 394186Notes

Reaction equation

HRID 394186 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[Br:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[C:14]([Br:21])[C:13]=1[CH2:22]Br.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[C:14]([Br:21])[C:13]=1[CH2:22][NH:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 22648021HCID 22648021, compound

Product 1

HCID 22648134HCID 22648134, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-methoxybenzylamine (2.15 g, 15.7 mmol) was added to a solution of 1,3-dibromo-2-(bromomethyl)-5-nitrobenzene (4.91 g, 13.1 mmol) in DMF (100 mL) under nitrogen at rt. K2CO3 (1.99 g, 14.4 mmol) was then added and the reaction mixture was stirred at rt overnight. The reaction mixture was quenched with 500 mL of water, and extracted with ethyl acetate (3×150 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The product was purified by flash chromatography on Biotage 40M columns, eluting with 90:10 hexanes-ethyl acetate to provide N-(2,6-dibromo-4-nitrobenzyl)-N-(4-methoxybenzyl)amine as a red viscous liquid. 1H NMR (500 MHz, CDCl3): δ 3.81 (d, J=3.6 Hz, 4H); 4.20 (s, 3H); 6.88 (d, J=8.4 Hz, 2H); 7.27 (d, J=5.9 Hz, 2H); 8.40 (s, 2H).

Workup

  1. customThe reaction mixture was quenched with 500 mL of water
  2. extractionextracted with ethyl acetate (3×150 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by flash chromatography on Biotage 40M columns
  7. washeluting with 90:10 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-7740d8caf48c464882b75820ec3d97c9
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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