반응 #45548

반응 방정식

7-bromo-2-tert-butyl-6-(2-furyl)-5-methyl-1,3-benzoxazole-4-carbonitrile

(3S)-3-(dimethylamino)pyrrolidine

sodium tert-butoxide

(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl

→

compound

수율 13.5%

2-tert-Butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-(2-furyl)-5-methyl-1,3-benzoxazole-4-Carbonitrile

수율 13.5%

용매

brine

toluene

toluene

반응 조건

후처리

1. 1
   온도under heat
2. 2
   workup.STIRRINGby stirring at 80° C. for 17 hours
3. 3
   온도After cooling
4. 4
   추출the product was extracted with chloroform (30 ml×3)
5. 5
   세척The organic layer was washed with saturated brine (30 ml)
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The residue was purified by silica gel column chromatography (chloroform:methanol=1:0→100:1)

실험 절차

(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (10.4 mg, 16.7 μmol) was dissolved in toluene (0.5 ml) under heat, cooled to room temperature, palladium(II) acetate (2.5 mg, 11.1 μmol) was added, followed by stirring for 1 minute. This was put into a toluene (0.5 ml) suspension of 7-bromo-2-tert-butyl-6-(2-furyl)-5-methyl-1,3-benzoxazole-4-carbonitrile (I-10) (40 mg, 111 μmol), (3S)-3-(dimethylamino)pyrrolidine (16.9 μl, 134 μmol), sodium tert-butoxide (15.0 mg, 156 μmol), followed by stirring at 80° C. for 17 hours. After cooling, brine (30 ml) was added to the reaction liquid, the product was extracted with chloroform (30 ml×3). The organic layer was washed with saturated brine (30 ml), then dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=1:0→100:1) to obtain the entitled compound (5.9 mg, 13%) as a yellow solid.

출처