3-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → (S)-5'-Fluoro-2-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-((trifluoromethyl)thio)phenyl)-[3,3'-bipyridine]-5-carboxamide

HRID 924045Notes

Reaction equation

HRID 924045 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@H:24]([CH2:27][OH:28])[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].[F:29][C:30]1[CH:31]=[N:32][CH:33]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:35]=1>>[F:29][C:30]1[CH:35]=[C:34]([C:2]2[C:3]([N:22]3[CH2:26][CH2:25][C@H:24]([CH2:27][OH:28])[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:19])[F:18])=[CH:12][CH:11]=3)=[O:8])[CH:21]=2)[CH:33]=[N:32][CH:31]=1

Participants

3

Reactant 2

HCID 164142683-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 86702606(S)-5-bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide

Product 1

HCID 118195180(S)-5'-Fluoro-2-(3-(hydroxymethyl)pyrrolidin-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 185 using (S)-5-bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide (Stage 189.1) and 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine. HPLC (Condition 4) tR=5.49 min, UPLC-MS (Condition 3) tR=1.10 min, m/z=493.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.45-1.64 (m, 1H) 1.76-1.92 (m, 1H) 2.14-2.28 (m, 1H) 2.88-3.02 (m, 1H) 3.11-3.40 (m, 5H) 4.60 (t, J=1.00 Hz, 1H) 7.67 (d, J=8.60 Hz, 2H) 7.79-7.85 (m, 1H) 7.90 (d, J=8.60 Hz, 2H) 8.06 (d, J=1.96 Hz, 1H) 8.50 (s, 1H) 8.57 (d, J=2.74 Hz, 1H) 8.77 (d, J=2.35 Hz, 1H) 10.26 (s, 1H).

Sources & evidence

ORD record
ord-9269e271e7a8459b915f585585a133fb
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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