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

HRID 12976

Reaction equation

HRID 12976 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][N:18]1[CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:20]=[N:19]1.C([C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=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:34]4[CH:39]=[CH:38][C:37]([C:21]5[CH:20]=[N:19][N:18]([CH3:17])[CH:22]=5)=[CH:36][CH:35]=4)=[CH:3][CH:4]=3)[CH2:12][CH2:11]2)[CH2:15]1

Participants

4

Reactant 3

HCID 27343264-Cyanophenylboronic acidHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 44221503(3aR,6aR)-1-(4-Bromophenyl)-5-methyloctahydropyrrolo[3,4-b]pyrrole

Product 1

HCID 24743846(3aR,6aR)-5-methyl-1-[4'-(1-methyl-1H-pyrazol-4-yl)-1,1'-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 1-methyl-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 7.78 (s, 1H) 7.62 (s, 1H) 7.45-7.60 (m, 6H) 6.65 (d, J=8.82 Hz, 2H) 4.11-4.21 (m, 1H) 3.95 (s, 3H) 3.50-3.61 (m, 1H) 3.23-3.35 (m, 1H) 2.90-3.05 (m, 1H) 2.69-2.77 (m, 1H) 2.50-2.69 (m, 3H) 2.33 (s, 3H) 2.11-2.26 (m, 1H) 1.88-2.02 (m, 1H). MS: (M+H)+=359.

Sources & evidence

ORD record
ord-174af34fb9b046739197326587d4787d
Source dataset
uspto-grants-2010_06
Patent number
US07728031B2

Linked notes

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