Potassium Carbonate → (RS)-4-[1-(4-pyridin-3-yl-but-3-enyl)-pyrrolidine-3-sulfonyl]-phenol

HRID 1280729Notes

Reaction equation

[CH2:1]([N:5]1[CH2:9][CH2:8][CH:7]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:6]1)[CH2:2][CH:3]=[CH2:4].Br[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:23]1[CH:24]=[CH:25][CH:26]=[C:21]([CH:4]=[CH:3][CH2:2][CH2:1][N:5]2[CH2:9][CH2:8][CH:7]([S:10]([C:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)(=[O:12])=[O:11])[CH2:6]2)[CH:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

(RS)-4-(1-But-3-enyl-pyrrolidine-3-sulfonyl)-phenol (100 mg, 0.355 mmol), 3-bromopyridine (62 mg, 0.39 mmol), PdCl2(dppf)2-dichloromethane complex (9.3 mg, 0.01 mmol), and K2CO3 (95 mg, 0.69 mmol) were suspended in DMF (1.5 ml). After 5 hours stirring at 80° C., the reaction mixture was cooled to room temperature and concentrated. The residue was chromatographed over silica gel (CH2Cl2/MeOH 97:3 then 19/1) to provide (RS)-4-[1-(4-pyridin-3-yl-but-3-enyl)-pyrrolidine-3-sulfonyl]-phenol (100 mg, 78%) as a light orange foam, MS: m/e=359.2 (M+H+).

Workup

temperaturethe reaction mixture was cooled to room temperature
concentrationconcentrated
customThe residue was chromatographed over silica gel (CH2Cl2/MeOH 97:3

Sources & evidence

ORD record: ord-ea9add34d3b948f4a7d9c22d97f2c887
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451819B2

Reaction notes

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