1,2-Dimethoxyethane → 5-Bromo-2-(4-(phenylsulfonyl)phenyl)pyridine

HRID 1972360Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)O1.Br[C:26]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+].COCCOC>CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CO.O>[Br:32][C:29]1[CH:30]=[CH:31][C:26]([C:9]2[CH:10]=[CH:11][C:12]([S:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)(=[O:16])=[O:17])=[CH:13][CH:14]=2)=[N:27][CH:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A 100 ml, pressure vessel was charged with 4,4,5,5-tetramethyl-2-(4-(phenylsulfonyl)phenyl)-1,3,2-dioxaborolane (1.00 g, 2.91 mmol), 2,5-dibromopyridine (0.860 g, 3.63 mmol, Sigma-Aldrich, St. Louis, Mo.), potassium carbonate (1.20 g, 8.72 mmol), tetrakis(triphenylphosphine)palladium (0) (0.168 g, 0.145 mmol, Strem Chemical Inc, Newburyport, Mass.), 16 mL of 1,2-dimethoxyethane, and 4 mL of water. The vessel was sealed and the reaction was heated at 100° C. for 2 h. After cooling to room temperature, the mixture was diluted with EtOAc (30 mL), separated, dried (MgSO4) and concentrated to give an oil. Purification via column chromatography (40 g of silica gel, 0 to 50% EtOAc in hexanes) produced a yellow solid that was slurried with cold (0° C.) MeOH (20 mL) to give 5-bromo-2-(4-(phenylsulfonyl)phenyl)pyridine (0.450 g).

Workup

customThe vessel was sealed
temperatureAfter cooling to room temperature
customseparated
dry with materialdried (MgSO4)
concentrationconcentrated
customto give an oil
customPurification via column chromatography (40 g of silica gel, 0 to 50% EtOAc in hexanes)
customproduced a yellow solid

Sources & evidence

ORD record: ord-e9ca048d589f41efb93dd9e710322e5e
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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