4-Cyanophenylboronic acid → 5-{4'-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1'-biphenyl-4-yl}pyridine-2-carbonitrile

HRID 12975Notes

Reaction equation

HRID 12975 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]=[CH:27][C:28]([C:31]#[N:32])=[N:29][CH:30]=2)O1.C([C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=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:36]4[CH:41]=[CH:40][C:39]([C:25]5[CH:26]=[CH:27][C:28]([C:31]#[N:32])=[N:29][CH:30]=5)=[CH:38][CH:37]=4)=[CH:3][CH:4]=3)[CH2:12][CH2:11]2)[CH2:15]1

Participants

4

Reactant 3

HCID 27343264-Cyanophenylboronic acidHCID 164141882-Cyanopyridine-5-boronic acid pinacol esterHCID 44221503(3aR,6aR)-1-(4-Bromophenyl)-5-methyloctahydropyrrolo[3,4-b]pyrrole

Product 1

HCID 247438175-{4'-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1'-biphenyl-4-yl}pyridine-2-carbonitrile

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 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile for 4-cyanophenylboronic acid. 1H NMR (500 MHz, CDCl3) δ ppm 8.99 (d, J=2.14 Hz, 1H) 8.03 (dd, J=8.09, 2.29 Hz, 1H) 7.76 (d, J=7.93 Hz, 1H) 7.68-7.73 (m, 2H) 7.59-7.67 (m, 2H) 7.52-7.58 (m, 2H) 6.67 (d, J=8.85 Hz, 2H) 4.12-4.23 (m, 3.05 Hz, 1H) 3.53-3.62 (m, 1H) 3.26-3.35 (m, 1H) 2.92-3.03 (m, 1H) 2.69-2.78 (m, 1H) 2.48-2.67 (m, 3H) 2.33 (s, 3H) 2.13-2.25 (m, 1H) 1.91-2.03 (m, 1H).

Sources & evidence

ORD record
ord-008e78b0f73a47f3a4efa79bc050a11b
Source dataset
uspto-grants-2010_06
Patent number
US07728031B2

Reaction notes

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