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

HRID 12977Notes

Reaction equation

HRID 12977 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.[CH3:17][C:18]1[C:22](B2OC(C)(C)C(C)(C)O2)=[C:21]([CH3:32])[NH:20][N:19]=1.C([C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)#N>>[CH3:32][C:21]1[C:22]([C:35]2[CH:40]=[CH:39][C:38]([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:37][CH:36]=2)=[C:18]([CH3:17])[NH:19][N:20]=1

Participants

4

Reactant 3

HCID 27343264-Cyanophenylboronic acidHCID 162177133,5-Dimethylpyrazole-4-boronic acid, pinacol esterHCID 44221503(3aR,6aR)-1-(4-Bromophenyl)-5-methyloctahydropyrrolo[3,4-b]pyrrole

Product 1

HCID 24743847(3aR,6aR)-1-[4'-(3,5-dimethyl-1H-pyrazol-4-yl)-1,1'-biphenyl-4-yl]-5-methyloctahydropyrrolo[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 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 4-cyanophenylboronic acid. 1H NMR (300 MHz, CDCl3) δ ppm 7.59 (d, J=8.14 Hz, 2H) 7.52 (d, J=8.82 Hz, 2H) 7.30 (d, J=8.14 Hz, 2H) 6.66 (d, J=8.82 Hz, 2H) 4.11-4.23 (m, 1H) 3.51-3.62 (m, 1H) 3.24-3.36 (m, 1H) 2.88-3.04 (m, 1H) 2.70-2.79 (m, 1H) 2.49-2.66 (m, 3H) 2.33 (s, 9H) 2.10-2.25 (m, 1H) 1.90-2.03 (m, 1H). MS: (M+H)+=373.

Sources & evidence

ORD record
ord-e8e631a076b7431491f579fbadbe6be2
Source dataset
uspto-grants-2010_06
Patent number
US07728031B2

Reaction notes

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