4-Bromo-2-fluorobenzeneboronic acid → (R)-(4-(6-Amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-YL)-3-fluorophenyl)dimethylphosphine oxide

HRID 1845857Notes

Reaction equation

HRID 1845857 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)=[C:24]([F:31])[CH:23]=1.[CH3:32][PH:33](=[O:35])[CH3:34]>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:25]2[CH:26]=[CH:27][C:22]([P:33]([CH3:34])([CH3:32])=[O:35])=[CH:23][C:24]=2[F:31])[CH:3]=1)[CH3:11]

Participants

5

Reactant 3

HCID 27733334-Bromo-2-fluorobenzeneboronic acidHCID 11689426(R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amineHCID 178503022methylphosphonoylmethane

Product 1

HCID 60168720(R)-(4-(6-Amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-YL)-3-fluorophenyl)dimethylphosphine oxide

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-bromo-2-fluoro-phenylboronic acid, and dimethylphosphine oxide followed the same procedures as Example 1 Step 1 and Step 3; ESMS: m/z 471 (M+H)+; chiral purity 93.12% (column AD-H 4.6*250 mm 5 um; solvent:hexane/isopropanol).

Sources & evidence

ORD record
ord-8b4bcbdb2336434fab511bf38242c7e5
Source dataset
uspto-grants-2015_02
Patent number
US08951993B2

Reaction notes

Loading…