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

HRID 1845855Notes

Reaction equation

HRID 1845855 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:9][C@@H: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]>CCCCCC.C(O)(C)C>[Cl:20][C:13]1[C:14]([F:19])=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[C@H: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)[CH:3]=1)[CH3:11]

Participants

5

Reactant 3

HCID 79599(4-Bromophenyl)boronic acidHCID 11689426(R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amineHCID 178503022methylphosphonoylmethane

Product 1

HCID 601687193-[(1R)-1-(2,6-dichloro-3-fluoro-phenyl)ethoxy]-5-(4-dimethylphosphorylphenyl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 21585144Isopropanol hexaneSolvent

Procedure

The title compound was prepared from 5-bromo-3-[(1R)-1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-2-ylamine, 4-bromophenyl boronic acid, and dimethylphosphine oxide following the same procedures as Example 1 Step 1 and Step 3; ESMS: m/z 453 (M+H)+; chiral purity 99.87% (column AD-H 4.6*250 mm 5 um; solvent:hexane/isopropanol).

Sources & evidence

ORD record
ord-a75d6145b9f84351b4b56e37e90507e4
Source dataset
uspto-grants-2015_02
Patent number
US08951993B2

Reaction notes

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