Reaction #682059

Reaction equation

K2CO3

N-{[6-bromo-4-(1,1-difluoro-2-hydroxyethyl)-4H-spiro[chromene-3,1′-cyclopropan]-4-yl]carbamothioyl}benzamide

1-chloro-N,N,2-trimethylprop-1-en-1-amine

→

N-(6′-bromo-5″,5″-difluoro-5″,6″-dihydrodispiro[cyclopropane-1,3′-chromene-4′,4″-[1,3]thiazin]-2″-yl)benzamide

Yield 60.4%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   workup.ADDITIONIce was added
2. 2
   Extractionextracted with CH2Cl2
3. 3
   WashThe organic layer was washed with brine
4. 4
   Dryingdried over MgSO4
5. 5
   Concentrationconcentrated
6. 6
   OtherThe residue was purified by silica gel chromatography (EtOAc/hexane=1:99-40:60)

Procedure

Under ice cooling, to a solution of N-{[6-bromo-4-(1,1-difluoro-2-hydroxyethyl)-4H-spiro[chromene-3,1′-cyclopropan]-4-yl]carbamothioyl}benzamide (340 mg, 0.684 mmol) in CH2Cl2 (9 mL) was added 1-chloro-N,N,2-trimethylprop-1-en-1-amine (206 mg, 1.54 mmol), and the mixture was stirred for 17 hours at room temperature. Ice was added and the mixture was neutralized by 10% aqueous K2CO3 and extracted with CH2Cl2. The organic layer was washed with brine and dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (EtOAc/hexane=1:99-40:60) to afford N-(6′-bromo-5″,5″-difluoro-5″,6″-dihydrodispiro[cyclopropane-1,3′-chromene-4′,4″-[1,3]thiazin]-2″-yl)benzamide (198 mg).

Source