تفاعل #1704060

معادلة التفاعل

1-difluoromethyl-7-iodo-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-C]pyridine

(2,3-difluorophenylsulfanyl)-triisopropylsilane

CsF

ethylene glycol

DMF

→

product

المردود 135.5%

1-(Difluoromethyl)-7-[(2,3-difluorophenyl)sulfanyl]-1-methyl-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridine

المردود 135.5%

ظروف التفاعل

المعالجة

1. 1
   أخرىInto a Schlenk flask equipped with a magnetic stir bar
2. 2
   أخرىThe Schlenck flask was evacuated
3. 3
   أخرىflushed with argon three times
4. 4
   درجة الحرارةUpon cooling
5. 5
   workup.ADDITIONthe reaction was diluted with DCM
6. 6
   ترشيحfiltered through celite and solvent
7. 7
   أخرىwas evaporated
8. 8
   أخرىPurification
9. 9
   غسيلTLC (2000 micron silica gfel plate; elution with 15% EtOAc in dichloromethane)

الإجراء التجريبي

Into a Schlenk flask equipped with a magnetic stir bar was added 1-difluoromethyl-7-iodo-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-C]pyridine (enantiomer 1, 100 mg, 0.30 mmol), (2,3-difluorophenylsulfanyl)-triisopropylsilane (125 mg, 0.43 mmol), CsF (189 mg, 1.24 mmol), CuI (25 mg, 0.13 mmol), ethylene glycol (85 μL, 1.5 mmol) and anhydrous DMF (3 mL, 0.30 mmol). The Schlenck flask was evacuated and flushed with argon three times. The reaction mixture was heated at 105° C. under argon for 17 h. Upon cooling, the reaction was diluted with DCM, filtered through celite and solvent was evaporated. Purification using preparative TLC (2000 micron silica gfel plate; elution with 15% EtOAc in dichloromethane) afforded 155 mg of product as a viscous, pale oil. MS m/z: 382 [M+H]+.

المصدر