Sodium Carbonate → 4-(2-Phenyl-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine

HRID 1603571Notes

Reaction equation

HRID 1603571 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.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.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>[C:23]1([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:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 69186894-(2-Bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamine

Product 1

HCID 196054794-(2-Phenyl-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamineYield 68.5%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 191 mg (0.5 mmole) 4-(2-bromo-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine, 60.9 mg (0.5 mmole) benzene-boronic acid, 55 mg sodium carbonate and 18 mg bis(triphenylphosphine)-palladium(II)-chloride is refluxed for 18 hours in 5 ml 1,2-dimethoxyethane and 0.25 ml water. The solvent is removed and the residue is diluted with dichloromethane. The dichloromethane solution is washed twice with water, dried over magnesiumsulfate and concentrated in vacuo. Flash chromatography (silicagel, ethyl acetate/hexane 1/1) of the residue yields 130 mg (68%) pure 4-(2-phenyl-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine as a pale yellow soild mp.: 255-258° C.

Workup

  1. customThe solvent is removed
  2. additionthe residue is diluted with dichloromethane
  3. washThe dichloromethane solution is washed twice with water
  4. dry with materialdried over magnesiumsulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c7c883199614553824d18f033ed1e19
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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