1,8-Diazabicyclo(5.4.0)undec-7-ene → N-(5-bromo-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

HRID 473084Notes

Reaction equation

HRID 473084 reaction equation
[CH3:1][CH:2]([S:4](Cl)(=[O:6])=[O:5])[CH3:3].[Br:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH:14]([NH2:18])[CH2:13][CH2:12]2.N12CCCN=C1CCCCC2>C(Cl)Cl>[Br:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH:14]([NH:18][S:4]([CH:2]([CH3:3])[CH3:1])(=[O:6])=[O:5])[CH2:13][CH2:12]2

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 824082-Propanesulfonyl chlorideHCID 222283885-bromo-2,3-dihydro-1H-inden-1-amine

Product 1

HCID 66733842N-(5-bromo-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At 0° C. and under protective atmosphere, a solution of 2-Propanesulfonyl chloride (11.87 mL, 121 mmol) in DCM (121 mL) was added gradually to a solution of 5-bromo-2,3-dihydro-1H-inden-1-amine (12.8 g, 60.4 mmol) and 1,8-Diazabicyclo[5.4.0]undec-7-ene (4.83 mL, 32.1 mmol) in Dichloromethane (300 mL). The reaction was stirred at rt overnight. The reaction mixture was washed with 1N KHSO4 (1×) and sat NaHCO3 (2×) before being dried on Na2SO4 and solvent evaporated in vacuo to afford a green oil. Purification by column chromatography (25% EtOAc in heptane) afforded the title compound as a white solid.

Workup

  1. washThe reaction mixture was washed with 1N KHSO4 (1×)
  2. custombefore being dried on Na2SO4 and solvent
  3. customevaporated in vacuo
  4. customto afford a green oil
  5. customPurification by column chromatography (25% EtOAc in heptane)

Sources & evidence

ORD record
ord-4ddbd9f065c34534acf79cf95b38bfcb
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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