Cyclopropylamine → 4-Bromo-N-cyclopropyl-2-fluorobenzene-1-sulfonamide

HRID 2239464Notes

Reaction equation

HRID 2239464 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[C:4]([F:12])[CH:3]=1.[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])=[C:4]([F:12])[CH:3]=1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 27363104-Bromo-2-fluorobenzene-1-sulfonyl chloride

Product 1

HCID 534399264-Bromo-N-cyclopropyl-2-fluorobenzene-1-sulfonamideYield 44.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to general procedure C, 4-Bromo-2-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-2-fluorobenzenesulfonamide (190 mg, 44%) was provided after purification. MS (ESI) m/z 294. HPLC purity 98.6% at 210-370 nm, 10.2 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-634d0b943f85494abc8e41877d027723
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

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