(4-Bromophenyl)boronic acid → 3-[1-(2,6-Dichloro-3-fluoro-phenyl)ethoxy]-5-(4-dimethylphosphorylphenyl)pyrazin-2-amine

HRID 1845840Notes

Reaction equation

Br[C:2]1[N: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][CH:23]=1.[CH3:31][PH:32](=[O:34])[CH3:33]>>[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:22]2[CH:27]=[CH:26][C:25]([P:32]([CH3:33])([CH3:31])=[O:34])=[CH:24][CH:23]=2)[N:3]=1)[CH3:11]

Participants

Reactant 3

HCID 79599(4-Bromophenyl)boronic acid

HCID 21111477HCID 21111477, compound

HCID 178503022methylphosphonoylmethane

Product 1

HCID 681941573-[1-(2,6-Dichloro-3-fluoro-phenyl)ethoxy]-5-(4-dimethylphosphorylphenyl)pyrazin-2-amine

Procedure

The title compound was prepared from 5-bromo-3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyrazin-2-ylamine, 4-bromophenylboronic acid, and dimethylphosphine oxide following the same procedures as Example 1 Step 1 and Step 3; ESMS: m/z 454 (M+H)+.

Sources & evidence

ORD record: ord-dccdff2b7de44821a91dc3b4cbaafe44
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08951993B2

Reaction notes

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