Sodium Carbonate → HCID 19605545, compound

HRID 1603575Notes

Reaction equation

HRID 1603575 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]([F:39])([F:38])[C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=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>[F:23][C:24]([F:38])([F:39])[C:25]1[CH:26]=[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:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 1562653,5-Bis-trifluoromethylphenylboronic acidHCID 69186894-(2-Bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamine

Product 1

HCID 19605545HCID 19605545, compoundYield 32.6%

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, 142 mg (0.55 mmole) 3,5-bis(trifluormethyl)phenylboronic acid, 25 mg sodium carbonate and 20 mg bis(triphenylphosphine)-palladium(II)-chloride is refluxed for 48 hours in 10 ml 1,2-dimethoxyethane and 1 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 84 mg (32%) pure 4-[2-(3,5-bis-trifluoromethyl-phenyl)-6-pyrrolidine-1-yl-pyridine-4-sulfonyl]-phenylamine as a pale yellow solid mp.: 184-186° 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-54ad291573e6402a8e6bcd30395ea911
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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