Cyclopropylamine → 4-Bromo-N-cyclopropyl-3-fluorobenzenesulfonamide

HRID 2239454Notes

Reaction equation

HRID 2239454 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12].[CH:13]1([NH2:16])[CH2:15][CH2:14]1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:16][CH:13]2[CH2:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 27782184-Bromo-3-fluorobenzenesulfonyl chloride

Product 1

HCID 684813974-Bromo-N-cyclopropyl-3-fluorobenzenesulfonamideYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to general procedure C, 4-Bromo-3-fluoro-benzenesulfonyl chloride (0.40 g, 1.46 mmol) and cyclopropylamine (0.25 mL, 3.65 mmol) were stirred together with dry dichloromethane (5 mL) for 16 hours. 4-bromo-N-cyclopropyl-3-fluorobenzenesulfonamide (0.37 g, 86%) was provided after purification. HRMS: calcd for C9H9BrFNO2S−H+, 291.94486; found (ESI, [M−H]−), 291.9462. HPLC purity 100.0% at 210-370 nm, 9.8 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/ACN+MeOH) for 10 min., hold 4 min.

Sources & evidence

ORD record
ord-9803137289384c30802adc3fe541b183
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

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