Triethylamine → N-(3-Fluoro-5-iodo-phenyl)-methanesulfonamide

Dissolve 3-fluoro-5-iodoaniline (600 mg, 2.53 mmol) (prepared as described in published PCT International Application WO96/23783 A1, published Aug. 8, 1996), methanesulfonyl chloride (896 mg, 7.83 mmol), triethylamine (1.91 g, 18.9 mmol), and N,N-dimethylamino-4-pyridine (31 mg, 0.253 mmol) in CH2Cl2 (10 mL) and stir at room temperature overnight. Dilute with 1.00N aqueous HCl (20 mL) and extract into ethyl acetate. Dry (MgSO4) and concentrate organics to a yellow solid. Dissolve solid in THF (50 mL) and add 1.0M tetrabutylammonium fluoride (2.8 mL). Heat to reflux for 3.5 h. Cool to room temperature, dilute with H2O, and extract into ethyl acetate. Dry (MgSO4) and concentrate organics. Chromatograph on silica gel (40 g), eluting with 20% to 35% ethyl acetate/hexanes affords 618 mg (78%) of the title compound as a white solid. MS (ES) 314 (M−H); HPLC shows 100% purity.

1. extractionextract into ethyl acetate
2. dry with materialDry (MgSO4)
3. concentrationconcentrate organics to a yellow solid
4. dissolutionDissolve solid in THF (50 mL)
5. additionadd 1.0M tetrabutylammonium fluoride (2.8 mL)
6. temperatureHeat
7. temperatureto reflux for 3.5 h
8. temperatureCool to room temperature
9. additiondilute with H2O
10. extractionextract into ethyl acetate
11. dry with materialDry (MgSO4)
12. concentrationconcentrate organics
13. washChromatograph on silica gel (40 g), eluting with 20% to 35% ethyl acetate/hexanes

ORD record

ord-c86df6b91b1b46949fdcf62f5e55b9cd

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07411072B2