(3-Chlorophenyl)boronic acid → HCID 19605452, compound

HRID 1603579Notes

Reaction equation

HRID 1603579 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.[Cl:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=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>[Cl:23][C:24]1[CH:29]=[C:28]([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:27]=[CH:26][CH:25]=1

Participants

6

Reactant 2

HCID 2734323(3-Chlorophenyl)boronic acidHCID 69186894-(2-Bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamine

Product 1

HCID 19605452HCID 19605452, compoundYield 22.7%

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, 84 mg (0.55 mmole) 3-chlorophenylboronic 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 47 mg (22%) pure 4-[2-(3-chloro-phenyl)-6-pyrrolidine-1-yl-pyridine-4-sulfonyl]-phenylamine as a pale yellow solid mp.: 260-261° C.

Workup

  1. customThe solvents are removed in vacuo

Sources & evidence

ORD record
ord-c246957a1a29499784305945152b7bf1
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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