반응 #9644

반응 방정식

Na2CO3

Methyl trans-2-(4-bromobenzoyl)cyclopentanecarboxylate

4-aminophenyl boronic acid

dichloromethane

→

methyl trans-2-[(4′-amino-1,1′-biphenyl-4-yl)carbonyl]-cyclopentanecarboxylate

수율 67.4%

용매

EtOAc

EtOH

Toluene

반응 조건

후처리

1. 1
   기타resulting solution
2. 2
   기타was degassed for 30 minutes
3. 3
   온도The mixture was cooled to it
4. 4
   기타The solvent was removed by rotary evaporation
5. 5
   workup.ADDITIONWater and EtOAc were added
6. 6
   추출the aqueous layer was extracted with EtOAc
7. 7
   세척The combined organic phases were washed with water, brine
8. 8
   건조dried over anhydrous sodium sulfate
9. 9
   여과filtered
10. 10
    농축concentrated in vacuo
11. 11
    기타The residue was purified by flash chromatography (Biotage Flash 40M)

실험 절차

Methyl trans-2-(4-bromobenzoyl)cyclopentanecarboxylate (1.60 g, 5.14 mmol) and 4-aminophenyl boronic acid (1.07 g, 6.17 mmol) were combined in a dry flask under argon. Toluene (25 mL), EtOH (10 mL), and 3 M aqueous Na2CO3 (8.50 mL, 25 mmol) were added and resulting solution was degassed for 30 minutes by using a flow of argon. Then [1,1′-bis(diphenylphosphino)-ferrocene]dichloro palladium(II), 1:1 complex with dichloromethane (419.9 mg, 0.51 mmol), was added and the resulting mixture was heated at 85° C. for 16 h. The mixture was cooled to it, diluted with EtOAc, and passed through a Celite® pad. The solvent was removed by rotary evaporation. Water and EtOAc were added and the aqueous layer was extracted with EtOAc. The combined organic phases were washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (Biotage Flash 40M) using 29 to 33% ethyl acetate in hexane to afford methyl trans-2-[(4′-amino-1,1′-biphenyl-4-yl)carbonyl]-cyclopentanecarboxylate (1.12 g, 67%). 1H NMR (400 MHz, CD2Cl2) δ 1.71–1.97 (m, 4H), 2.17 (m, 2H), 3.44 (m, 1H), 3.65 (s, 3H), 4.12 (m, 1H), 6.84 (m, 2H), 7.51 (m, 2H), 7.66 (m, 2H), 8.00 (m, 2H).

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