Phosphine → HCID 89704803, compound

HRID 928927Notes

Reaction equation

HRID 928927 reaction equation
Br[C:2]1[C:3]([F:21])=[C:4]([F:20])[C:5]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].P.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][SH:32])=[CH:27][CH:26]=1>[Pd]>[F:20][C:4]1[C:5]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[C:6]([CH:11]=[C:2]([S:32][CH2:31][C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)[C:3]=1[F:21])[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 24404PhosphineHCID 804074-Methoxy-alpha-toluenethiolHCID 59519391Methyl 5-bromo-2-(2-fluorophenylamino)-3,4-difluorobenzoate

Product 1

HCID 89704803HCID 89704803, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of methyl 5-bromo-3,4-difluoro-2-((2-fluorophenyl)amino)benzoate in appropriate solvent is added base under nitrogen atmosphere, followed by Pd catalyst, phosphine ligand and (4-methoxyphenyl)methanethiol. The reaction is generally carried out at high temperature (80-130° C., prefer 90-110° C.) and normally complete within several hours (8-24 h, prefer 12-18 h). Methyl 3,4-difluoro-2-((2-fluorophenyl)amino)-5-((4-methoxybenzyl)thio)benzoate is obtained after conventional workup.

Workup

  1. customis generally carried out at high temperature (80-130° C., prefer 90-110° C.)
  2. waitnormally complete within several hours
  3. custom(8-24 h, prefer 12-18 h)

Sources & evidence

ORD record
ord-1f857e7e702d413bb9c3d2ddf5f24b96
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

Loading…