4-Bromo-3-fluorobenzeneboronic acid → 3-[1-(2,6-Dichloro-3-fluoro-phenyl)ethoxy]-5-(4-dimethylphosphoryl-3-fluoro-phenyl)pyridin-2-amine

HRID 1845843Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([O:9][CH:10]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[C:14]([F:19])[C:13]=2[Cl:20])[CH3:11])[C:5]([NH2:8])=[N:6][CH:7]=1.Br[C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][C:23]=1[F:31].[CH3:32][PH:33](=[O:35])[CH3:34]>>[Cl:20][C:13]1[C:14]([F:19])=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[CH:10]([O:9][C:4]1[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:25]2[CH:26]=[CH:27][C:22]([P:33]([CH3:34])([CH3:32])=[O:35])=[C:23]([F:31])[CH:24]=2)[CH:3]=1)[CH3:11]

Participants

Reactant 3

HCID 27733354-Bromo-3-fluorobenzeneboronic acid

HCID 211114785-Bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine

HCID 178503022methylphosphonoylmethane

Product 1

HCID 601685283-[1-(2,6-Dichloro-3-fluoro-phenyl)ethoxy]-5-(4-dimethylphosphoryl-3-fluoro-phenyl)pyridin-2-amine

Procedure

The title compound was prepared from 5-bromo-3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-2-ylamine, 4-bromo-3-fluoro-phenyl boronic acid, and dimethylphosphine oxide following the same procedures as Example 1 Step 1 and Step 3; ESMS: m/z 471 (M+H)+.

Sources & evidence

ORD record: ord-3cfc4b8547654f26bf28443d46052d8f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08951993B2

Reaction notes

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