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

HRID 12978Notes

Reaction equation

HRID 12978 reaction equation
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.CC1(C)C(C)(C)OB([C:25]2[CH:26]=[N:27][N:28]([C:30]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:29]=2)O1.C([C:52]1[CH:57]=[CH:56][C:55](B(O)O)=[CH:54][CH:53]=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:52]4[CH:57]=[CH:56][C:55]([C:25]5[CH:26]=[N:27][N:28]([C:30]([C:31]6[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=6)([C:43]6[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=6)[C:37]6[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=6)[CH:29]=5)=[CH:54][CH:53]=4)=[CH:3][CH:4]=3)[CH2:12][CH2:11]2)[CH2:15]1

Participants

4

Reactant 3

HCID 27343264-Cyanophenylboronic acidHCID 44221503(3aR,6aR)-1-(4-Bromophenyl)-5-methyloctahydropyrrolo[3,4-b]pyrroleHCID 457896834-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H-pyrazole

Product 1

HCID 68495764(3aR,6aR)-5-methyl-1-(4'-(1-trityl-1H-pyrazol-4-yl)biphenyl-4-yl)octahydropyrrolo[3,4-b]pyrrole

Procedure

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 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-pyrazole for 4-cyanophenylboronic acid. 1H NMR (300 MHz, CDCl3) δ ppm 7.96 (s, 1H) 7.63 (s, 1H) 7.42-7.54 (m, 6H) 7.29-7.37 (m, 9H) 7.17-7.24 (m, 6H) 6.64 (d, J=8.82 Hz, 2H) 4.11-4.23 (m, 1H) 3.49-3.61 (m, 1H) 3.23-3.35 (m, 1H) 2.91-3.03 (m, 1H) 2.66-2.78 (m, 1H) 2.51-2.66 (m, 3H) 2.33 (s, 3H) 2.12-2.24 (m, 1H) 1.92-2.01 (m, 1H). MS: (M+H)+=586.

Sources & evidence

ORD record
ord-2bd5433b4f754d08a3ecb052c01270d8
Source dataset
uspto-grants-2010_06
Patent number
US07728031B2

Reaction notes

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