Allyl bromide → HCID 67024036, compound

HRID 450735Notes

Reaction equation

HRID 450735 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH2:16][CH:17]([CH2:23][NH2:24])[CH2:18]3)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH2:25](Br)[CH:26]=[CH2:27].C(N(CC)CC)C>CN(C=O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH2:16][CH:17]([CH2:23][NH:24][CH2:27][CH:26]=[CH2:25])[CH2:18]3)(=[O:12])=[O:11])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8471TriethylamineHCID 67024027HCID 67024027, compound

Product 1

HCID 67024036HCID 67024036, compoundYield 11.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Isopropyl-N-(2-aminomethyl-indan-4-yl)-benzenesulfonamide (80 mg, 0.23 mmol), allyl bromide (30 mg, 0.23 mmol) and triethylamine (20 mg, 0.23 mmol) were dissolved in 2 mL of DMF and stirred at room temperature for 18 h. The solution was concentrated, water added and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and the filtrate was evaporated in vacuo to give a residue which was purified by column chromatography using (dichloromethane-MeOH, 0-5%) to give a yellow oil (10 mg, 6%).

Workup

  1. concentrationThe solution was concentrated
  2. additionwater added
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customthe filtrate was evaporated in vacuo
  7. customto give a residue which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-efb7ddbb0aae49fa95ab355fca95bee6
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Reaction notes

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