5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile → (R)-5'-Cyano-2-(3-hydroxypyrrolidin-1-yl)-N-(4-((trifluoromethyl)thio)phenyl)-[3,3'-bipyridine]-5-carboxamide

HRID 924042Notes

Reaction equation

HRID 924042 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].CC1(C)C(C)(C)OB([C:36]2[CH:37]=[N:38][CH:39]=[C:40]([CH:43]=2)[C:41]#[N:42])O1>>[C:41]([C:40]1[CH:43]=[C:36]([C:2]2[C:3]([N:22]3[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]3)=[N:4][CH:5]=[C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([S:16][C:17]([F:20])([F:18])[F:19])=[CH:12][CH:11]=3)=[O:8])[CH:21]=2)[CH:37]=[N:38][CH:39]=1)#[N:42]

Participants

3

Reactant 2

HCID 164142165-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrileHCID 86702604(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide

Product 1

HCID 118195105(R)-5'-Cyano-2-(3-hydroxypyrrolidin-1-yl)-N-(4-((trifluoromethyl)thio)phenyl)-[3,3'-bipyridine]-5-carboxamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 151 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide (Stage 186.1) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile to afford a beige solid. UPLC-MS (Condition 3) tR=1.06 min, m/z=486.1 [M+H]+, m/z=484.4 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.69-1.79 (m, 1H) 1.80-1.92 (m, 1H) 2.85 (d, J=11.29 Hz, 1H) 3.16-3.27 (m, 2H) 3.35-3.43 (m, 1H) 4.18-4.25 (m, 1H) 4.90 (d, J=3.64 Hz, 1H) 7.70 (d, J=8.78 Hz, 2H) 7.88-7.96 (m, 2H) 8.10 (d, J=2.38 Hz, 1H) 8.41 (t, J=2.07 Hz, 1H) 8.80 (d, J=2.38 Hz, 1H) 8.91 (d, J=2.13 Hz, 1H) 9.03 (d, J=1.88 Hz, 1H) 10.29 (s, 1H).

Workup

  1. customto afford a beige solid

Sources & evidence

ORD record
ord-59c62ad8c60a45ada684b5ad9442f06f
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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