4-Fluorophenylboronic acid → 4-[2-(4-Fluoro-phenyl)-6-pyrrolidine-1-yl-pyridine-4-sulfonyl]-phenylamine

HRID 1603577Notes

Reaction equation

HRID 1603577 reaction equation
Br[C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[C:4]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[N:3]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[CH:7]=[C:6]([S:8]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)(=[O:10])=[O:9])[CH:5]=[C:4]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[N:3]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 69186894-(2-Bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamine

Product 1

HCID 196054874-[2-(4-Fluoro-phenyl)-6-pyrrolidine-1-yl-pyridine-4-sulfonyl]-phenylamineYield 22.6%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 11430Potassium CarbonateSolvent

Procedure

A mixture of 191 mg (0.5 mmole) 4-(2-bromo-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine, 77 mg (0.55 mmole) 4-fluorophenylboronic acid, 18 mg bis(triphenylphosphine)-palladium(II)-chloride is refluxed for 2 hours in 7 ml toluene and 2 ml 2N aqueous potassium carbonate. The solvents are removed in vacuo. Flash chromatography (silicagel, ethyl acetate/hexane 1/1) of the residue yields 45 mg (22%) pure 4-[2-(4-fluoro-phenyl)-6-pyrrolidine-1-yl-pyridine-4-sulfonyl]-phenylamine as a white solid mp.: 245-246° C.

Workup

  1. customThe solvents are removed in vacuo

Sources & evidence

ORD record
ord-29e881c601d04c41974bbbf4d93ad25f
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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