4-(2-Bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamine → 4-(2-Cyclohex-1-enyl-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine

HRID 1603570Notes

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([Sn](CCCC)(CCCC)[C:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]=1)CCC>CN(C)C=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:28]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)[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 382 mg (1 mmole) 4-(2-bromo-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine, 371 mg (1 mmole) tributyl-cyclohex-1-enyl stannane, and 70 mg bis(triphenylphosphine)-palladium(II)-chloride in 20 ml dimethylformamide is stirred for 3 hours at 80° C. The solvent is removed and the residue is diluted with dichloromethane. The dichloromethane solution is washed twice with saturated aqueous potassium fluoride, dried over magnesiumsulfate and concentrated in vacuo. Flash chromatography of the residue (silicagel, hexane/AcOEt 3/1) yields 191 mg (50%) pure 4-(2-cyclohex-1-enyl-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine as a white solid. mp 237-238° C.

Workup

customThe solvent is removed
additionthe residue is diluted with dichloromethane
washThe dichloromethane solution is washed twice with saturated aqueous potassium fluoride
dry with materialdried over magnesiumsulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d2253be82abb4962b5795b4eda388938
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990105

Reaction notes

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