반응 #2156971

반응 방정식

6-Bromo-3,4-dihydro-2H-isoquinolin-1-one

cyclopropylboronic acid

→

6-Cyclopropyl-3,4-dihydro-2H-isoquinolin-1-one

수율 97.2%

용매

toluene

H2O

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled
2. 2
   여과filtered
3. 3
   세척washed with toluene
4. 4
   기타The organic phase was partitioned
5. 5
   세척washed with water and brine
6. 6
   건조dried over Na2SO4
7. 7
   여과filtered
8. 8
   농축concentrated to an oil
9. 9
   workup.ADDITIONAddition of hexanes

실험 절차

To a round bottomed flask charged with 6-Bromo-3,4-dihydro-2H-isoquinolin-1-one (16.9 g, 74.7 mmol), cyclopropylboronic acid (9.45 g, 1.5 equiv), tricyclohexylphosphine (1.04 mg, 0.025 equiv), and K3PO4 hexahydrate (50 g, 2 equiv) in toluene (210 mL) and H2O (15 mL) was added Pd(OAc)2 (100 mg, 0.05 equiv).The combined mixture was heated for 4 h at 100° C. The reaction mixture was cooled, filtered and washed with toluene. The organic phase was partitioned and washed with water and brine, dried over Na2SO4, filtered and concentrated to an oil. Addition of hexanes produced 6-Cyclopropyl-3,4-dihydro-2H-isoquinolin-1-one as a tan solid (13.6 g). MS (ESI) 187.1 (M+H)+.

출처