Structure of 445491-71-4
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 445491-71-4 |
Formula : | C6H6BrNO2S |
M.W : | 236.09 |
SMILES Code : | O=S(C1=CN=CC(Br)=C1)(C)=O |
MDL No. : | MFCD09801057 |
InChI Key : | CNAIMMQZMLBREW-UHFFFAOYSA-N |
Pubchem ID : | 22391981 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; | d 3-Bromo-5-methanesulfonyl-pyridine MCPBA (9.2 g, 38 mmol) was added slowly to a solution of 3-bromo-5-methylsulfanyl-pyridine (3.8 g, 19 mmol) in dichloromethane (50 mL). After stirring for 30 minutes, the reaction was diluted with dichloromethane and quenched carefully with 1N NaOII. The product was extracted with dichloromethane and dried over magnesium sulfate. The solvent was removed under reduced pressure to give title compound (2.7 g, 82% yield) as a white solid. |
47% | With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 0.5h; | To a solution of 3-bromo-5-methanesulfanyl-pyridine (8.80 g, 43 mmol) in CH2Cl2 was treated slowly portionwise with 3-chloroperbenzoic acid (21.26 g, 86 mmol) at rt (exothermic reaction). The reaction mixture was stirred for 30 minutes at rt under Argon, then diluted with an additional portion of CH2Cl2 and washed with 1N NaOH solution. The aqueous layer was extracted with 3 portions of CH2Cl2 and the combined layers were dried over MgSO4, filtered and concentrated to give the title compound (4.75 g, 47%) as a white solid. MS (ISP) 236.1 [(M+H)+], 237.9[(M+2+H)+]. |
With Oxone; sodium hydrogencarbonate; In tetrahydrofuran; methanol; water; at 20℃; for 4.0h; | To 3,5-dibromopyridine (2.96 g, 12.5 mmol) in diethyl ether (70 ml) at -78 C. was added n-butyllithium 1.6M in hexanes (8.6 ml, 13.7 mmol) and the resulting mixture was stirred in the cold for 3 hours. Dimethyl disulfide (1.12 ml, 12.5 mmol) was added and the mixture was warmed to room temperature, then partitioned between ether and water. To the crude product from evaporation of the organic phase was added tetrahydrofuran (80 ml), methanol (20 ml), oxone (17 g) and enough saturated aqueous sodium bicarbonate to afford a slightly basic medium. After stirring for 4 hours at room temperature, an excess of 1M aqueous sodium metabisulfite was added, the organic solvents were evaporated, and the residue was partitioned between ethyl acetate and water. The crude product from the organic phase was stirred in a small volume of ethyl acetate and filtered to afford the 3-Bromo-5-methylsulfonylpyridine compound as a solid. |
With Oxone; In tetrahydrofuran; water; at 0 - 20℃; | Step 2) Formation of 3-bromo-5-(methylsulfonyl)pyridineTo a solution of 2-bromo-6-(methylthio)pyridine (10 g, 49.0 mmol) in THF (125 mL) was added oxone (30 g, 98.0 mmol) in water in a dropwise fashion at 00C and stirred at RT for 3 h. The mixture was extracted with EtOAc washed with water, brine, dried over Na2SO4, evaporated and purified by silica gel column chromatography (PE/EtOAc) to afford the title compound as a white solid. LC/MS, M+(ESI): 237.8.HPLC, Rt: 5.45 min (purity: 99.6%). 1H NMR (DMSO-d6, 400 MHz) delta 9.07-9.04 (m, 2H), 8.58 (s, 1 H), 3.39 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; oxone; In tetrahydrofuran; methanol; diethyl ether; ethyl acetate; | Step 2 3-Bromo-5-Methylsulfonylpyridine To 3,5-dibromopyridine (2.96 g, 12.5 mmol) in diethyl ether (70 ml) at -78 C. was added n-butyllithium 1.6M in hexanes (8.6 ml, 13.7 mmol) and the resulting mixture was stirred in the cold for 3 hours. Dimethyl disulfide (1.12 ml, 12.5 mmol) was added and the mixture was warmed to room temperature, then partitioned between ether and water. To the crude product from evaporation of the organic phase was added tetrahydrofuran (80 ml), methanol (20 ml), oxone (17 g) and enough saturated aqueous sodium bicarbonate to afford a slightly basic medium. After stirring for 4 hours at room temperature, an excess of 1M aqueous sodium metabisulfite was added, the organic solvents were evaporated, and the residue was partitioned between ethyl acetate and water. The crude product from the organic phase was stirred in a small volume of ethyl acetate and filtered to afford the 3-Bromo-5-methylsulfonylpyridine compound as a solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With triethylamine; In dichloromethane; | e 3-Methanesulfonyl-5-triethoxyprop-1-ynyl-pyridine A solution of <strong>[445491-71-4]3-bromo-5-methanesulfonyl-pyridine</strong> (1.00 g, 4.20 mmol), 3,3,3-triethoxypropyne (1.75 g, 9.4 mmol), dichlorobis(triphenylphospine)palladium(II) (0.15 g, 0.21 mmol), copper(I)iodide (0.08 g, 0.42 mmol), triethylamine (1.80 mL, 12.7 mmol) and dichloromethane (40 mL) was heated at reflux for 48 h. The mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude product was chromatographed on silica (30% ethyl acetate/hexanes) to give the title compound (1.2 g, 87% yield) as yellow solid. 1H NMR (CDCl3) delta9.08(d, 1H, J=2.4 Hz), 8.91 (d, 1H J=2.0), 8.28 (t, 1H, J=2.0 Hz), 3.75 (q, 6H, J=7.2), 3.13 (s, 3H), 1.29 (t, 9H, J=7.2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With copper(l) iodide; N,N-dimethylglycine hydrochoride; caesium carbonate; In 1,4-dioxane;Heating / reflux; | Example 196; 3-methyl-4-(3-[5-(methylsulfonyl)pyridin-3-yl]oxy}phenyl)-8- (trifluoromethyl)quinoline; 3-Bromo-5-(methanesulfonyl)pyridine (233 mg, 0.989 mmol, see, e.g., WO 2002/060438 for a description of the synthesis) was added to a mixture of 3 -[3 -methyl- 8-(trifluoromethyl)quinolin-4-yl]phenol (150 mg, 0.494 mmol), CuI (9 mg, 0.0494 mmol), N- N-dimethylglycine hydrochloride (25 mg, 0.185 mmol), Cs2CO3 (482 mg, 1.47 mmol) in 1,4- dioxane (5 mL). The reaction was heated at reflux overnight, then cooled and treated with water. The mixture was extracted with ethyl acetate and the combined organics dried over MgStheta4 and concentrated in vacuo. The residue was chromatographed to yield the title compound (140 mg, 62%) as a white solid. MS (ESI) m/z 459; HRMS: calcd for C23H17F3N2O3S + H+, 459.09847; found (ESI, [M+H]+), 459.1004. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With piperidine;bis-triphenylphosphine-palladium(II) chloride; In toluene; at 90℃; for 3.0h; | Example 367; 3-benzyl-4-(3-[5-(methylsulfonyl)pyridin-3-yl]ethynyl}phenyl)-8- (trifluoromethyl)quinolineA solution of 3-benzyl-4-(3-ethynyl-phenyl)-8-trifluoromethyl-quinoline (80 mg, 0.20 mmol), 3-bromopyridinemethylsulfone 93 mg, 0.40 mmol), piperidine (80 mg, 0.90 mmol) in toluene (2.0 mL) was treated with Pd(Cl)2(PPh3)2 (8.0 mg) and heated at 90 0C for 3 h. The reaction was then cooled and concentrated in vacuo. The residue was taken up in ethyl acetate and washed with IN aqueous HCl (10 mL). The organic layer was dried and concentrated in vacuo to provide after chromatography the title compound (75 mg, 70%). MS (ES) m/z 542.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With ammonia;copper(II) sulfate; In water; at 170℃; for 16.0h;Alkaline aqueous solution; | A mixture of <strong>[445491-71-4]3-bromo-5-(methylsulfonyl)pyridine</strong> (0.50 g, 2.1 mmol) and CuSO4-(H2O)5 (53 mg, 0.21 mmol) in concentrated ammonium hydroxide (3 mL) was heated in a sealed tube at 170 0C for 16 hours. The reaction was cooled to room temperature and extracted with ethyl acetate. The combined extracts were dried over sodium sulfate and evaporated to give a brown solid. The solid was purified by column chromatography on silica gel using 0-5% MeOH in dichloromethane to give 5-(methylsulfonyl)pyridin-3 -amine (0.11 g, 31% yield) as a tan solid. LC/MS: m/z 173.3 (M+H)+ at 0.21 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; ethanol; water; at 120℃; for 1.0h;Microwave irradiation; | Method 3; 5'-(methylsulfony])-3,3'-bipyridin-6-amineA suspension of 3-bromo-5-(trifluoromethyl)pyridine (2.0 g, 8.40 mmol) 2- Aminopyridine-5-boronic acid pinacol ester (1.94 g, 8.8 mmol), [ 1 , rbis(diphenylphosphino)ferrocene] dichloro-palladium (II) complex with CH2CI2 (136 mg, 0.17 mmol) and sodium carbonate (2.6 g, 25 mmol) in DMEiEbOiEtOH, (7:3:2, 2 mL) was heated to 120 0C for 1 hour minutes in the microwave. After this time the reaction solvents were removed in vacuo and the brown residue redissolved in 2M HCl (30 mL), the aqueous phase was washed with ethyl acetate (3 x 20 mL) and then neutralized with concentrated sodium hydroxide to pH 7.0. Ethyl acetate (20 mL) was added and the title compound collected by filtration and air-dried (1.95 g, 7.6 mmol, 91 %). No further purification was required. LCMS (method A) (M+H+) 250, Rt = 1.65 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With potassium acetate; tricyclohexylphosphine;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; at 100℃; for 5.0h; | Intermediate 61 : 3-(methylsulfonyl)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)pyridineA mixture of <strong>[445491-71-4]3-bromo-5-methanesulfonylpyridine</strong> (2 g, 8.47 mmol), bis(pinacolato)diboron (2.36 g, 9.31 mmol), potassium acetate (1.25 g, 12.7 mmol),Pd2dba3 (0.38 g, 0.42 mmol) and tricyclohexylphosphine (0.52 g, 1.86 mmol) in degassed dioxane was heated at 1000C for 5h. The reaction mixture was then diluted with EtOAc and washed with brine. Organic layer was dried over sodium sulfate, filtered and concentrated. The residue obtained was triturated in ether, ether layer was carefully removed and the solid was dried to give the title compound (1.82 g,75%). 1H NMR (DMSO-d6, 400MHz) delta 9.16(1 H, s), 9.01 (1 H, s), 8.39-8.40 (1 H, s), 3.34 (3H, s), 1.32 (12H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With cesium fluoride;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 80℃; for 12.0h; | Step 4} Formation of 6-[5~(methy.supsilonffonyi)pyridin~3-yi]-1 ,3-benzothiazo.-2-amine A mixture of 6~(4>;4,5.5-tetramethyl-1,3-dioxaborolan~2-yl}~1/3~benzothiazol~2~amine (5 g, 18 mmol), 3~bromo5~(methy.suifonyi)pyridine (4.27 g, 18 mmo.), cesium fluoride (5.5 g, 36.2 mmol) and PdCi2 (PPh3J2 (0.25 gs 0.4 mmol) in DMF (25 mL) stirred at800C for 12 h. The reaction mixture was cooied RT. poured into ice water and the product was extracted with ethyl acetate (2x10OmL). The combined organic layer was dried over Na2SO4 and evaporated under vacuum. The crude product was purified by column chromatography (CHCi3ZMeOH) to afford the titie compound (3.5 g, 64%) as paie yellow solid.LC/MS, M+(ESi): 305.9. HPLC1 Rt: 5.45 min (purity 99.6%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 150℃; for 0.333333h;Microwave irradiation; | To a mixture of 2-amino-N-iert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3- b]pyrazine-7-carboxamide (92 mg, 253 muiotaetaomicron), <strong>[445491-71-4]3-bromo-5-(methylsulfonyl)pyridine</strong> (77.7 mg, 329 muiotaetaomicron), xantphos (43.9 mg, 75.9 muiotaetaomicron), Pd2(dba)3 (23.2 mg, 25.3 muiotaetaomicron) and cesium carbonate (165 mg, 506 muiotaetaomicron) in dioxane (2 mL) was heated in a microwave at 150C for 20 min. The mixture was cooled then filtered through a pad of celite. The filtrate was concentrated in vacuo then purified by chromatography (silica, 30-70 % ethyl acetate in hexanes) to give N- iert-butyl-2-(5-(methylsulfonyl)pyridin-3-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H- pyrrolo[2,3-b]pyrazine-7-carboxamide (125 mg, 241 muiotaetaomicron, 95 %) as a yellow gum. (EI/CI) m/z 519.3 [M + H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | [00265] A solution of <strong>[445491-71-4]3-bromo-5-(methylsulfonyl)pyridine</strong> 1-oxide (250 mg, 1.06 mmol) wasdissolved in DCM (1.8 niL) and cooled to 0C. mCPBA (822 mg, 4.77 mmol) was added portionwise, and then allowed to wam to ii and stir overnight. The reaction mixture was concentrated and a 15%K2C03 solution was added and extracted with EtOAc. The combined organic layers were washed withbrine, dried over MgSO4 and concentrated by rotary evaporation. The crude compound was used without further purification. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | Step 1: <strong>[445491-71-4]3-bromo-5-(methylsulfonyl)pyridine</strong> 1-oxide A solution of <strong>[445491-71-4]3-bromo-5-(methylsulfonyl)pyridine</strong> 1-oxide (250 mg, 1.06 mmol) was dissolved in DCM (1.8 mL) and cooled to 0 C. mCPBA (822 mg, 4.77 mmol) was added portionwise, and then allowed to warm to rt and stir overnight. The reaction mixture was concentrated and a 15% K2CO3 solution was added and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and concentrated by rotary evaporation. The crude compound was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15 mg | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; ethanol; at 90℃; for 3.0h; | 5-(2,4-Difluoro-phenyl)-3-pentafluoroethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,5-dihydro-1H-pyrazole (30.0 mg, 0.06 mmol) prepared in Step 1,<strong>[445491-71-4]3-bromo-5-methanesulfonyl-pyridine</strong> (13.5 mg, 0.06 mmol), Pd(PPh3)4 (7.0 mg, cat.) and a 2N sodium carbonate solution (300.0 uL) were added to a mixed solvent of ethanol (300.0 uL) and 1,2-dimethoxyethane (1.0 mL). The reaction mixture was stirred at 90 C. for 3 hours and then filtered through celite pad. A saturated solution of ammonium chloride was added to the filtrate, which was then extracted with ethyl acetate three times. The combined extract was washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/6) to give 15.0 mg of the titled compound as a white liquid. (0672) 1H NMR (400 MHz, CDCl3) 9.11 (s, 1H), 8.99 (s, 1H), 8.28 (s, 1H), 7.35 (t, 1H), 7.27 (d, 1H), 7.18-7.12 (m, 2H), 7.01 (d, 1H), 6.95-6.86 (m, 2H), 5.71 (dd, 1H), 3.78 (dd, 1H), 3.16 (s, 3H), 3.04 (dd, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With copper(l) iodide; potassium carbonate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 115℃;Inert atmosphere; Sealed tube; | In a pressure tube, argon was bubbled through a suspension of 3,3-dimethyl-6-(2- methyl pyri m idin-5-y 1 )i ndol i n-2-onc (70 mg, 276 mu etaiotaomicron. Eq: 1, WO2014/202493 Al), 3-bromo- - (methylsulfonyl)pyridine (78.3 mg, 332 mupiiotaomicron, Eq: 1.2) and potassium carbonate (76.4 mg, 553 mupiiotaomicron, Eq: 2) in acetonitrile (1.11 ml) for 5 minutes. Then N,N'-dimethylethylenediamine (9.74 mg, 11.9 mu, 111 mupiiotaomicron, Eq: 0.4) and copper (I) iodide (10.5 mg, 55.3 mupiiotaomicron, Eq: 0.2) were added, again flused with argon, the tube was sealed and the reaction mixture was heated to 115 C overnight. The mixture was diluted with dichloromethane. (0197) The residue was purified by chromatography on silica gel to afford the desired product as a light yellow solid (116 mg, 99 %). MS (m/z) = 409.1 [(M+H)+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; caesium carbonate; In 1,4-dioxane; at 100℃; for 16.0h;Inert atmosphere; | A mixture of Pch(dba)3 (16 mg, 0.017 mmol) and BrettPhos (18 mg, 0.034 mmol) in l,4-dioxane (1 mL) was stirred at 50 C for 10 min. l-(3-Amino-5-methyl-5H- chromeno[4,3-c]pyridin-8-yl)pyrrolidin-2-one (50 mg, 0.17 mmol), 3-bromo-5- (methylsulfonyl)pyridine (48 mg, 0.20 mmol) in dioxane (3 mL) and CS2CO3 (165 mg, 0.508 mmol) were added and the resulting mixture was stirred at 100 C for 16 h. A black brown mixture was formed. LCMS (Rt = 0.615 min; MS Calcd: 450.1; MS Found: 451.0 [M+H]+). The reaction mixture was diluted with DCM (10 mL), filtered and concentrated. The residue was purified by prep-HPLC (0.05% NH32O as an additive) and lyophilized to give l-(5- methyl-3-((5-(methylsulfonyl)pyridin-3-yl)amino)-5H-chromeno[4,3-c]pyri din-8- yl)pyrrolidin-2-one (9.0 mg, yield: 12%) as a white solid. (1242) NMR (400 MHz, DMSO-r/e) d 1.55 (3H, d, J= 6.4 Hz), 2.02-2.09 (2H, m), 2.53 (2H, overlap with DMSO), 3.32 (3H, s), 3.85 (2H, t , J= 8.0 Hz), 5.32 (1H, q, J= 6.4 Hz), 6.80 (1H, s), 7.33 (1H, dd, J= 8.8, 2.4 Hz), 7.42 (1H, d, J= 2.4 Hz), 7.94 (1H, d , J= 8.8 Hz), 8.58 (1H, d, J= 2.0 Hz), 8.77 (1H, s), 8.88 (1H, t, J= 2.0 Hz), 9.03 (1H, d, J= 2.4 Hz), 9.95 (1H, brs). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A heterogeneous solution of compound 121-1 (0.1 g, 0.272 mmol,1 equiv.), bis(pinacolato)diboron (0.079 g, 0.31 mmol,1.2 equiv.), PdCl2(dppf) (0.011 g, 0.014 mmol, 0.05 equiv.), and KOAc (0.053 g, 0.545 mmol, 2 equiv.) in dioxane (4 mL) was degassed with argon and heated at 90 C overnight with vigorous stirring. The resulting black heterogenous mixture was cooled to rt and <strong>[445491-71-4]3-bromo-5-methanesulfonylpyridine</strong> (0.061 g, 0.258 mmol,1 equiv.), potassium carbonate (0.113 g, 0.817 mmol, 3 equiv.), and water (1 mL) were added to the reaction mixture. The reaction mixture was again degassed with argon and heated at 100 C for 4 h. Then the reaction mixture was cooled to rt and the solvent was removed under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent:0-2 % MeOH in dichloromethane) to give compound 121-2 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A heterogeneous solution of compound 100-1 (0.104 g, 0.283 mmol,1 equiv.), bis(pinacolato)diboron (0.108 g, 0.425 mmol,1.5 equiv.), PdCl2(dppf) (0.011 g, 0.014 mmol, 0.05 equiv.), and KOAc (0.056 g, 0.566 mmol, 2 equiv.) in 1,4-dioxane (4 mL) was degassed with argon and heated at 90 C overnight with vigorous stirring. The resulting black heterogenous mixture was cooled to rt and <strong>[445491-71-4]3-bromo-5-methanesulfonylpyridine</strong> (0.08 g, 0.34 mmol,1.2 equiv.), potassium carbonate (0.113 g, 0.817 mmol, 3 equiv.), and water (1 mL) were added to the reaction mixture. The reaction mixture was again degassed with argon and heated at 100 C for 4 h, then the reaction mixture was cooled to rt and the solvent was removed under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent:0-2 % MeOH in dichloromethane) to give compound 129-1 as a colorless resin. |