2-Chloro-3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → 6'-Chloro-5'-fluoro-2-(3-(hydroxymethyl)azetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

HRID 923974Notes

Reaction equation

HRID 923974 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:25][CH:24]([CH2:26][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]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[Cl:28][C:29]1[C:34]([F:35])=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][N:30]=1>>[Cl:28][C:29]1[N:30]=[CH:31][C:32]([C:2]2[C:3]([N:22]3[CH2:23][CH:24]([CH2:26][OH:27])[CH2:25]3)=[N:4][CH:5]=[C:6]([C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([O:16][C:17]([F:18])([F:20])[F:19])=[CH:14][CH:15]=3)=[O:8])[CH:21]=2)=[CH:33][C:34]=1[F:35]

Participants

3

Reactant 2

HCID 533985412-Chloro-3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 899079805-bromo-6-(3-(hydroxymethyl)azetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 899076196'-Chloro-5'-fluoro-2-(3-(hydroxymethyl)azetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 53 using 5-bromo-6-(3-(hydroxymethyl)azetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 135.1) and 2-chloro-3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine. HPLC (Condition 4) tR=5.57 min, UPLC-MS (Condition 3) tR=1.13 min, m/z=497.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.55-2.70 (m, 1H) 3.39-3.53 (m, 4H) 3.73 (t, J=1.00 Hz, 2H) 4.69 (t, J=1.00 Hz, 1H) 7.34 (d, J=8.21 Hz, 2H) 7.83 (m, J=9.40 Hz, 2H) 8.04 (d, J=1.95 Hz, 1H) 8.09 (m, J=9.40 Hz, 1H) 8.38 (d, J=1.95 Hz, 1H) 8.77 (d, J=2.35 Hz, 1H) 10.19 (s, 1H).

Sources & evidence

ORD record
ord-2d833d966cb24da594bce313c041dc2c
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

Loading…