4-Cyanophenylboronic acid → (3aR,6aR)-5-methyl-1-(4'-pyrimidin-5-yl-1,1'-biphenyl-4-yl)octahydropyrrolo[3,4-b]pyrrole

HRID 12959

Reaktionsgleichung

Reaktionsgleichung von HRID 12959
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.[N:17]1[CH:22]=[C:21](B(O)O)[CH:20]=[N:19][CH:18]=1.C([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)#N>>[CH3:16][N:14]1[CH2:13][C@@H:10]2[C@@H:9]([N:8]([C:5]3[CH:6]=[CH:7][C:2]([C:28]4[CH:33]=[CH:32][C:31]([C:21]5[CH:22]=[N:17][CH:18]=[N:19][CH:20]=5)=[CH:30][CH:29]=4)=[CH:3][CH:4]=3)[CH2:12][CH2:11]2)[CH2:15]1

Komponenten

4

Edukt 3

HCID 27343264-Cyanophenylboronic acidHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 44221503(3aR,6aR)-1-(4-Bromophenyl)-5-methyloctahydropyrrolo[3,4-b]pyrrole

Produkt 1

HCID 24743650(3aR,6aR)-5-methyl-1-(4'-pyrimidin-5-yl-1,1'-biphenyl-4-yl)octahydropyrrolo[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 pyrimidine-5-boronic acid for 4-cyanophenylboronic acid. 1H NMR (300 MHz, CDCl3) δ ppm 9.19 (s, 1H) 8.99 (s, 2H) 7.62-7.74 (m, 4H) 7.52-7.58 (m, 2H) 6.63-6.70 (m, 2H) 4.20-4.31 (m, 1H) 3.55-3.67 (m, 1H) 3.30-3.42 (m, 1H) 2.99-3.14 (m, 1H) 2.60-2.84 (m, 4H) 2.42 (s, 3H) 2.16-2.26 (m, 1H) 1.95-2.05 (m, 1H); MS (M+H)+=357.

Quellen und Nachweise

ORD-Eintrag
ord-77cd97a9d29b4edcae9d41b13b024132
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728031B2

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