Ethanesulfonamide → HCID 59578412, compound

HRID 391338Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[CH:5]=[N:6][CH:7]=1.[CH2:10]([S:12]([NH2:15])(=[O:14])=[O:13])[CH3:11].[F:16][C:17]1[CH:22]=[CH:21][C:20]([Mg]Br)=[CH:19][CH:18]=1>C1(C)C=CC=CC=1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)[NH:15][S:12]([CH2:10][CH3:11])(=[O:14])=[O:13])[CH:5]=[N:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-bromo-pyridine-3-carbaldehyde (0.930 g, 5 mmol), ethanesulfonamide (0.682 g, 6.25 mmol) and titanium(IV) isopropoxide (2.93 ml, 10.00 mmol) in toluene (10 mL) was heated to 100° C. for 4 h. After concentration, the residue was dissolved in THF (12.5 ml), and (4-fluorophenyl)magnesium bromide (1 M in THF, 12.50 mL, 12.50 mmol) was added dropwise at −78° C. The mixture was stirred at −78° C. for 45 min. The mixture was quenched with saturated NH4Cl and extracted with EtOAc two times, dried over magnesium sulfate, filtered, and concentrated. The residue was purified via Biotage (10-40% AcOEt/heptane; SNAP25 column) giving the title compound (986 mg, 53%) as a beige solid. LC-MS (M+1) 375.0.

Workup

concentrationAfter concentration
dissolutionthe residue was dissolved in THF (12.5 ml)
customThe mixture was quenched with saturated NH4Cl
extractionextracted with EtOAc two times
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified via Biotage (10-40% AcOEt/heptane; SNAP25 column)

Sources & evidence

ORD record: ord-13cb6355362641bba318453054f1869c
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383827B2

Reaction notes

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