Hexane → 2-Chloro-5'-fluoro-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

HRID 924110Notes

Reaction equation

HRID 924110 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.CCCCCC>C(Cl)Cl>[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

5

Reactant 3

HCID 8058HexaneHCID 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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in an analogous fashion to that described in Stage 223.1 using 6-chloro-5-iodo-N-(4-(trifluoromethoxy)phenyl)nicotinamide and 3-fluoropyridine-5-boronic acid pinacol ester. The crude product was dissolved in DCM (20 mL) and treated with n-hexane. The resulting solid was filtered off, washed with n-hexane and dried to afford the title product as a beige solid. UPLC-MS (Condition 3) tR=1.13 min, m/z=412 [M+H]+.

Workup

  1. customThe title compound was prepared in an analogous fashion to
  2. filtrationThe resulting solid was filtered off
  3. washwashed with n-hexane
  4. customdried

Sources & evidence

ORD record
ord-dc043d15a8934b67b13dec6c6c9abacf
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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