4-Cyanophenylboronic acid → (3aR,6aR)-1-[4'-(2-methoxypyrimidin-5-yl)-1,1'-biphenyl-4-yl]-5-methyloctahydropyrrolo[3,4-b]pyrrole

HRID 12974

Reaktionsgleichung

Reaktionsgleichung von HRID 12974
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][C@@H:10]3[CH2:13][N:14]([CH3:16])[CH2:15][C@H:9]23)=[CH:4][CH:3]=1.[CH3:17][O:18][C:19]1[N:24]=[CH:23][C:22](B(O)O)=[CH:21][N:20]=1.C([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)#N>>[CH3:17][O:18][C:19]1[N:24]=[CH:23][C:22]([C:30]2[CH:35]=[CH:34][C:33]([C:2]3[CH:7]=[CH:6][C:5]([N:8]4[CH2:12][CH2:11][C@@H:10]5[CH2:13][N:14]([CH3:16])[CH2:15][C@H:9]45)=[CH:4][CH:3]=3)=[CH:32][CH:31]=2)=[CH:21][N:20]=1

Komponenten

4

Edukt 3

HCID 27343264-Cyanophenylboronic acidHCID 27367782-Methoxypyrimidine-5-boronic acidHCID 44221503(3aR,6aR)-1-(4-Bromophenyl)-5-methyloctahydropyrrolo[3,4-b]pyrrole

Produkt 1

HCID 24743816(3aR,6aR)-1-[4'-(2-methoxypyrimidin-5-yl)-1,1'-biphenyl-4-yl]-5-methyloctahydropyrrolo[3,4-b]pyrrole

Versuchsvorschrift

The title compound was prepared according to the procedure described in Example 7D, substituting the product of Example 41A for the product of Example 7C and substituting 2-methoxy-pyrimidine-5-boronic acid for 4-cyanophenylboronic acid. 1H NMR (500 MHz, CDCl3) δ ppm 8.76 (s, 2H) 7.66 (d, J=8.54 Hz, 2H) 7.53 (dd, J=11.75, 8.70 Hz, 4H) 6.67 (d, J=8.85 Hz, 2H) 4.13-4.22 (m, 1H) 4.07 (s, 3H) 3.53-3.61 (m, 1H) 3.26-3.35 (m, 1H) 2.91-3.03 (m, 1H) 2.71-2.77 (m, 1H) 2.48-2.67 (m, 3H) 2.33 (s, 3H) 2.13-2.25 (m, 1H) 1.90-2.01(m, 1H). MS, (M+H)+=387.

Quellen und Nachweise

ORD-Eintrag
ord-7ec783b5cf594ccfb60f56e13e3479b9
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728031B2

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