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

HRID 629122Notes

Reaction equation

HRID 629122 reaction equation
[Cl:1][C:2]1[C:21](I)=[CH:20][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[F:23][C:24]1[CH:25]=[N:26][CH:27]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH:29]=1>>[Cl:1][C:2]1[C:21]([C:28]2[CH:27]=[N:26][CH:25]=[C:24]([F:23])[CH:29]=2)=[CH:20][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 164142683-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 867025996-chloro-5-iodo-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 722015862-Chloro-5'-fluoro-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 56 using 6-chloro-5-iodo-N-(4-(trifluoromethoxy)phenyl)nicotinamide and 3-fluoropyridine-5-boronic acid pinacol ester to afford the title product as a beige solid. UPLC-MS (Condition 2) tR=1.13 min, m/z=412 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.39 (d, J=8.99 Hz, 2H) 7.85 (d, J=8.99 Hz, 2H) 8.02-8.12 (m, 1H) 8.49 (d, J=2.35 Hz, 1H) 8.64-8.76 (m, 2H) 8.99 (dd, J=2.35, 0.78 Hz, 1H) 10.65 (s, 1H).

Workup

  1. customThe title compound was prepared in an analogous fashion to

Sources & evidence

ORD record
ord-aae2fc1a1fd84ab0b9913ccb7beb6646
Source dataset
uspto-grants-2016_04
Patent number
US09315489B2

Reaction notes

Loading…