4-bromo-N-tert-butyl-N-methylbenzenesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Bromo-N-(tert-butyl)benzenesulfonyl amide (100 mg, 0.342 mmol) and potassium carbonate (95 mg, 0.684 mmol) were dissolved in DMF (2 ml), followed by addition of iodomethane (0.043 ml, 0.684 mmol), and then the resulting liquid was stirred at room temperature for 18 hours. Distilled water (10 ml) was added to the resulting reaction liquid, followed by extraction with EtOAc (10 ml×3). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (20% EtOAc/Hexanes), to obtain 77 mg of yellow oil (73%). followed by extraction with EtOAc (10 ml×3) The organic layer was dried over anhydrous sodium sulfate followed by filtration and concentration the residue thus obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Bromo-N-(tert-butyl)benzenesulfonyl amide (100 mg, 0.342 mmol) and potassium carbonate (95 mg, 0.684 mmol) were dissolved in DMF (2 ml), followed by addition of iodomethane (0.043 ml, 0.684 mmol), and then the resulting liquid was stirred at room temperature for 18 hours. Distilled water (10 ml) was added to the resulting reaction liquid, followed by extraction with EtOAc (10 ml×3). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (20% EtOAc/Hexanes), to obtain 77 mg of yellow oil (73%). followed by extraction with EtOAc (10 ml×3) The organic layer was dried over anhydrous sodium sulfate followed by filtration and concentration the residue thus obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Procedure S′: 4′-(tert-Butyl-methyl-sulfamoyl)-biphenyl-4-carboxylic acid methyl ester is prepared in a manner substantially analogous to Procedure O′ using 4-bromo-N-tert-butyl-N-methyl-benzenesulfonamide (459 mg, 1.5 mmol), 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (CAS 17136-80-0) (490 mg, 1.87 mmol), tricyclohexylphosphine (65 mg, 0.23 mmol), Pd(OAc)2 (34 mg, 0.15 mmol), and CsF (906 mg, 6 mmol) to give the intermediate 4′-(tert-Butyl-methyl-sulfamoyl)-biphenyl-4-carboxylic acid methyl ester (350 mg, 65% yield). MS (ES+) 384.1 (M+Na)+ Procedure S′: 4′-(tert-Butyl-methyl-sulfamoyl)-biphenyl-4-carboxylic acid methyl ester is prepared in a manner substantially analogous to Procedure O′

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Procedure R′: A 15 m-1L DMF mixture of 4-bromo-N-tert-butyl-benzenesulfonamide (1022 mg, 3.5 mmol), iodomethane (0.44 mL, 7 mmol), and K2CO3 (987 mg, 7 mmol) is stirred at room temperature overnight. Water and ethyl acetate are added to the mixture. The aqueous layer is extracted several times with ethyl acetate. The combined organic layers are washed with H2O and brine, then dried over Na2SO4 and evaporated. The crude product is purified by silica-gel column chromatography (gradient: 100% CH2Cl2 to 20% EtOAc/CH2Cl2) give the intermediate 4-bromo-N-tert-butyl-N-methyl-benzenesulfonamide (1040 mg, 97% yield). MS (ES+) 251.9 (M-tBu)+, NMR (CDCl3). The aqueous layer is extracted several times with ethyl acetate The combined organic layers are washed with H2O and brine dried over Na2SO4 evaporated The crude product is purified by silica-gel column chromatography (gradient: 100% CH2Cl2 to 20% EtOAc/CH2Cl2)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Procedure S′: 4′-(tert-Butyl-methyl-sulfamoyl)-biphenyl-4-carboxylic acid methyl ester is prepared in a manner substantially analogous to Procedure O′ using 4-bromo-N-tert-butyl-N-methyl-benzenesulfonamide (459 mg, 1.5 mmol), 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (CAS 17136-80-0) (490 mg, 1.87 mmol), tricyclohexylphosphine (65 mg, 0.23 mmol), Pd(OAc)2 (34 mg, 0.15 mmol), and CsF (906 mg, 6 mmol) to give the intermediate 4′-(tert-Butyl-methyl-sulfamoyl)-biphenyl-4-carboxylic acid methyl ester (350 mg, 65% yield). MS (ES+) 384.1 (M+Na)+ Procedure S′: 4′-(tert-Butyl-methyl-sulfamoyl)-biphenyl-4-carboxylic acid methyl ester is prepared in a manner substantially analogous to Procedure O′

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Procedure R′: A 15 mL DMF mixture of 4-bromo-N-tert-butyl-benzenesulfonamide (1022 mg, 3.5 mmol), iodomethane (0.44 mL, 7 mmol), and K2CO3 (987 mg, 7 mmol) is stirred at room temperature overnight. Water and ethyl acetate are added to the mixture. The aqueous layer is extracted several times with ethyl acetate. The combined organic layers are washed with H2O and brine, then dried over Na2SO4 and evaporated. The crude product is purified by silica-gel column chromatography (gradient: 100% CH2Cl2 to 20% EtOAc/CH2Cl2) give the intermediate 4-bromo-N-tert-butyl-N-methyl-benzenesulfonamide (1040 mg, 97% yield). MS (ES+) 251.9 (M-tBu)+, NMR (CDCl3). The aqueous layer is extracted several times with ethyl acetate The combined organic layers are washed with H2O and brine dried over Na2SO4 evaporated The crude product is purified by silica-gel column chromatography (gradient: 100% CH2Cl2 to 20% EtOAc/CH2Cl2)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Bromo-N-(tert-butyl)benzenesulfonyl amide (100 mg, 0.342 mmol) and potassium carbonate (95 mg, 0.684 mmol) were dissolved in DMF (2 ml), followed by addition of iodomethane (0.043 ml, 0.684 mmol), and then the resulting liquid was stirred at room temperature for 18 hours. Distilled water (10 ml) was added to the resulting reaction liquid, followed by extraction with EtOAc (10 ml×3). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (20% EtOAc/Hexanes), to obtain 77 mg of yellow oil (73%). followed by extraction with EtOAc (10 ml×3) The organic layer was dried over anhydrous sodium sulfate followed by filtration and concentration the residue thus obtained