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Structure of 25194-01-8 * Storage: {[proInfo.prStorage]}
* 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.
With hydrogenchloride; iron In ethanol; water at 95℃; for 16 h;
(3) 2,6-dichloropyridine-4-amine To a solution of 2,6-dichloro-4-nitropyridine (14.82 g, 76.79 mmol) in 350 mL ethanol were sequentially added iron powder (19.91 g, 356.58 mmol), water (65.8 mL, 3.6 mol) and concentrated hydrochloric acid (14.1 mL, 464.1 mmol). After the reaction was performed by stirring for 16 h at 95° C., the reaction solution was cooled to room temperature, adjusted to neutral pH, and subjected to suction filtration. After the filtrate was concentrated, it was extracted with ethyl acetate. The organic phase was combined, dried with anhydrous MgSO4, and subjected to rotary evaporation to afford 11.9 g titled product with a yield of 95.1percent.
95.1%
With hydrogenchloride; water; iron In ethanol at 95℃; for 16 h;
(3) 2,6-dichloropyridine-4-amine To a solution of 2,6-dichloro-4-nitropyridine (14.82 g, 76.79 mmol) in 350 mL ethanol were sequentially added iron powder (19.91 g, 356.58 mmol), water (65.8 mL, 3.6 mol) and concentrated hydrochloric acid (14.1 mL, 464.1 mmol). After the reaction was performed by stirring for 16 h at 95 °C, the reaction solution was cooled to room temperature, adjusted to neutral pH, and subjected to suction filtration. After the filtrate was concentrated, it was extracted with ethyl acetate. The organic phase was combined, dried with anhydrous MgSO4, and subjected to rotary evaporation to afford 11.9 g titled product with a yield of 95.1percent.
Reference：
[1] Patent: US2012/289497, 2012, A1, . Location in patent: Page/Page column 51-52
[2] Patent: EP2524917, 2012, A1, . Location in patent: Page/Page column 58-59
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 3, p. 1511 - 1530
[4] Nucleosides, Nucleotides and Nucleic Acids, 2003, vol. 22, # 12, p. 2133 - 2144
[5] ChemCatChem, 2016, vol. 8, # 8, p. 1485 - 1489
[6] ChemCatChem, 2017, vol. 9, # 19, p. 3743 - 3751
Reference：
[1] Nucleosides, Nucleotides and Nucleic Acids, 2003, vol. 22, # 12, p. 2133 - 2144
[2] Nucleosides, Nucleotides and Nucleic Acids, 2003, vol. 22, # 12, p. 2133 - 2144
6
[ 1826-67-1 ]
[ 25194-01-8 ]
[ 67139-79-1 ]
Yield
Reaction Conditions
Operation in experiment
1.4%
at -78℃; for 1 h;
Step A: 4,6-dichloro-1 H-pyrrolor3,2-clpyridine: 2,6-dichloro-4-nitro-pyridine (1 1 g, 57 mmol) was dissolved in dry tetrahydrofurane (300 ml_), cooled to -78°C and treated dropwise with bromo(vinyl)magnesium (1 M in THF, 200 ml_, 200 mmol). The reaction was allowed to react at this temperature for 1 hour and then allowed to warm to -20°C. The reaction mixture was then quenched with 200 ml of aqueous NH4CI and the mixture obtained was partitioned in ethyl acetate. The aqueous layer was extracted 3 times with 200 ml of ethyl acetate and the combined organic layer dried over Na2S04, filtered and concentrated in vacuo. Purification by Combi flash chromatography with a column of 120g and a gradient cyclohexane:0-100percent ethyl acetate, and then with a column of 40 g and a gradient dichloromethane:0-10percent ethyl acetate gave the title compound as brown solid (0.150 g, 1 .4percent).
Step 1: A mixture of 2,6-dichloro-4-nitropyridine (1.0 equiv.), potassium carbonate (3 equiv.) and methanol (20 equiv.) were heated to 70° C. for 25 min in the microwave. The reaction mixture was diluted with methanol and was decanted from remaining solids. After concentration, the mixture was partitioned between water and EtOAc. The organic phase was washed with brine and dried over sodium sulfate. The solution was concentrated and dried under vacuo to give 2,6-dichloro-4-methoxypyridine in 88percent yield. LCMS (m/z) (M+H)=177.9/179.9, Rt=0.72 min.
Reference：
[1] Patent: US2014/275003, 2014, A1, . Location in patent: Paragraph 0700; 0701
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 5, p. 1940 - 1943
8
[ 25194-01-8 ]
[ 17228-75-0 ]
Reference：
[1] Patent: US5624942, 1997, A,
[2] Patent: US5691277, 1997, A,
Stage #1: With sulfuric acid; nitric acid In water at 148 - 156℃; for 1 h; Stage #2: With ammonia In water
(2) 2,6-dichloro-4-nitropyridine To a solution of 95percent concentrated nitric acid (21 mL) and 98percent concentrated sulfuric acid (50 mL) was added 2,6-dichloropyridine-N-oxide (12.8 g, 78 mmol). After the reaction was performed at 148° C. by stirring for 1 h, it was continued when the temperature was increased to 156° C. until no nitrogen dioxide was released. The reaction solution was cooled to room temperature, poured into 150 g ice water, and adjusted to pH=6 with ammonia water to precipitate a solid product. It was subjected to suction filtration. The resultant crude product was recrystallized with petroleum ether to afford 10 g yellow solid with a yield of 66.4percent.
66.4%
Stage #1: at 148 - 156℃; for 1 h; Stage #2: With ammonia In water at 20℃;
(2) 2,6-dichloro-4-nitropyridine To a solution of 95percent concentrated nitric acid (21 mL) and 98percent concentrated sulfuric acid (50 mL) was added 2,6-dichloropyridine-N-oxide (12.8 g, 78 mmol). After the reaction was performed at 148°C by stirring for 1 h, it was continued when the temperature was increased to 156 °C until no nitrogen dioxide was released. The reaction solution was cooled to room temperature, poured into 150 g ice water, and adjusted to pH = 6 with ammonia water to precipitate a solid product. It was subjected to suction filtration. The resultant crude product was recrystallized with petroleum ether to afford 10 g yellow solid with a yield of 66.4percent.
With hydrogenchloride; iron; In ethanol; water; at 95℃; for 16h;
(3) 2,6-dichloropyridine-4-amine To a solution of <strong>[25194-01-8]2,6-dichloro-4-nitropyridine</strong> (14.82 g, 76.79 mmol) in 350 mL ethanol were sequentially added iron powder (19.91 g, 356.58 mmol), water (65.8 mL, 3.6 mol) and concentrated hydrochloric acid (14.1 mL, 464.1 mmol). After the reaction was performed by stirring for 16 h at 95 C., the reaction solution was cooled to room temperature, adjusted to neutral pH, and subjected to suction filtration. After the filtrate was concentrated, it was extracted with ethyl acetate. The organic phase was combined, dried with anhydrous MgSO4, and subjected to rotary evaporation to afford 11.9 g titled product with a yield of 95.1%.
95.1%
With hydrogenchloride; water; iron; In ethanol; at 95℃; for 16h;
(3) 2,6-dichloropyridine-4-amine To a solution of <strong>[25194-01-8]2,6-dichloro-4-nitropyridine</strong> (14.82 g, 76.79 mmol) in 350 mL ethanol were sequentially added iron powder (19.91 g, 356.58 mmol), water (65.8 mL, 3.6 mol) and concentrated hydrochloric acid (14.1 mL, 464.1 mmol). After the reaction was performed by stirring for 16 h at 95 C, the reaction solution was cooled to room temperature, adjusted to neutral pH, and subjected to suction filtration. After the filtrate was concentrated, it was extracted with ethyl acetate. The organic phase was combined, dried with anhydrous MgSO4, and subjected to rotary evaporation to afford 11.9 g titled product with a yield of 95.1%.
EXAMPLE 2 Preparation of 2,6-di-(3-trifluoromethylphenoxy)-4-methylthiopyridine To a solution of <strong>[25194-01-8]2,6-dichloro-4-nitropyridine</strong> (3.8 g; 0.02 mol) in dimethylformamide (50 ml) cooled with an ice-bath was sodium thiomethoxide (1.4 g; 0.02 mol) slowly added. After stirring for 3 hours, the reaction mixture was quenched with water (300 ml) and extracted 3 times each with a hexane/ethyl acetate mixture (100 ml; 1/1). The combined extracts were dried with anhydrous magnesium sulphate and the solvent was removed in vacuo. Purification by silica gel flash column chromatography afforded 2,6-dichloro-4-methylthiopyridine (2.9 g; 74%) as a colorless oil. A mixture of 2,6-dichloro-4-methylthiopyridine (0.97 g; 0.005 mol), 3-hydroxybenzotrifluoride (1.3 ml; 10.4 mmol) and sodium hydride (0.2 g) was reacted and worked up according to the procedure of Example 1 above to give 2,6-di-(3-trifluoromethyl phenoxy)-4-methylthiopyridine (1.9 g; 85%)
2,4-Bis-(1"-methyl-3"-trifluoromethylpyrazol-5"-yloxy)-6-(4'-trifluoromethylphenyl)pyridine[ No CAS ]
[ 202995-56-0 ]
Yield
Reaction Conditions
Operation in experiment
With potassium carbonate; In sulfolane;
2,4-Bis-(1"-methyl-3"-trifluoromethylpyrazol-5"-yloxy)-6-(4'-trifluoromethylphenyl)pyridine A mixture of <strong>[25194-01-8]4-nitro-2,6-dichloropyridine</strong> (3.9 g, 20 mmol), 1-methyl-3-trifluoromethyl-5-hydroxypyrazole (7.3 g, 44 mmol) and potassium carbonate (6.7 g, 48 mmol) in anhydrous sulfolane is heated to 110 C. overnight. The reaction mixture is cooled to ambient temperature, diluted with pentane/ethyl acetate (volume ratio of 1:1) and filtered through a bed of silica gel. The filtrate is washed 10 times with water, dried over anhydrous magnesium sulfate and the solvents are removed in vacuo. The residue is purified by flash silica gel chromatography using pentane/ethyl acetate. One obtains 2,4-bis-(1'-methyl-3'-trifluoromethylpyrazol-5'-yloxy)-6-chloropyridine (4.3 g, m.p. 105 C.).
2,6-Dichloro-4-(2,5-dichloro-4-methylmercapto-phenoxy)-pyridine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In water; acetone;
(b) 2,6-Dichloro-4-(2,5-dichloro-4-methylmercaptophenoxy)-pyridine Quantities of 19.3 gm (0.1 mol) of <strong>[25194-01-8]2,6-dichloro-4-nitropyridine</strong> and 23.1 gm (0.11 mol) of 2,5-dichloro-4-methylmercaptophenol were dissolved in 100 ml of acetone, 13.8 gm (0.1 mol) of K2 CO3 were added, and the resulting mixture was stirred for 3 hours under reflux. It was then stirred into 500 ml of water, and the precipitate formed was recovered by suction filtration. Yield: 32.5 gm (91.5% of theory). M.p.: 144-146 C. Analysis: C12 H7 Cl4 NOS (355.08) Calc.: C 40.59 H 1.99, N 3.95; Found: C 40.78 H 2.30, N 3.85.
With anhydrous phosphorus trichloride; In 1,2-dichloro-ethane;
(a) 2,6-Dichloro-4-nitropyridine A solution of 20.9 gm (0.1 mol) of 2,6-dichloro-4-nitropyridine-1-oxide (J. Chem. Soc. B 1967, 1235) in 100 ml of ethylene chloride was heated to boiling and then 27.5 gm (0.2 mol) of phosphorus trichloride were added. The solution obtained was stirred for a further 8 hours under reflux and was then concentrated by evaporation in vacuo. The oily residue which remained was poured into ice water. The crystalline residue formed was recovered by suction filtration and washed neutral with water. Yield: 17.5 gm (91% of theory). M.p.: 98-99 C. Analysis: C5 H2 Cl2 N2 O2 (193) Calc.: C 31.11, H 1.04, N 14.52; Found: C 31.31, H 1.30, N 14.38.
With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 1h;Inert atmosphere; Sealed tube;
PREPARATION 27; ferf-Butyl 4-(4-amino-6^[4^trifluoromethyl)pyridin-2-yl]amino}-2,4'-bipyridin-2'- yl)piperazine-1 -carboxy late; a) 6-Chloro^-nitro-W-[4-(trifluoromethyl)pyridin-2-yl]pyridin-2-amine; An oven dried resealable Schlenk tube was charged with <strong>[25194-01-8]2,6-dichloro-4-nitropyridine</strong> (0.75 g, 3.89 mmol), 4-(trifluoromethyl)pyridin-2-amine (0.63 g, 3.89 mmol), cesium carbonate (1.52 g, 4.66 mmol) and 1 ,4-dioxane (9 ml_). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and tris(dibenzylideneacetone)dipalladium(0) (0.07 g, 0.08 mmol) and 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (0.09 g, 0.15 mmol) were added. After three further cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in an oil bath at 100 C. After 1h, the mixture was cooled, filtered through Celite and the solvent was removed in vacuo. The residue was purified by flash chromatography (gradient from 100% hexane to 80% ethyl acetate) to give the title compound (1.01 g, 84%) as a solid.LRMS (m/z): 319/321 (M+1)+.1H NMR (400 MHz, CHLOROFORM-c delta ppm 7.21 (d, =4.80 Hz, 1 H) 7.52 (s, 1 H) 7.63 (s, 1 H) 7.86 (s, 1 H) 8.53 (d, J=4.80 Hz, 1 H) 8.63 (s, 1 H)
84%
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane;Inert atmosphere; Schlenk technique;
An oven dried resealable Schlenk tube was charged with <strong>[25194-01-8]2,6-dichloro-4-nitropyridine</strong> (0.75 g, 3.89 mmol), 4-(trifluoromethyl)pyridin-2-amine (0.63 g, 3.89 mmol), cesium carbonate (1.52 g, 4.66 mmol) and 1,4-dioxane (9 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and tris(dibenzylideneacetone)dipalladium(0) (0.07 g, 0.08 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.09 g, 0.15 mmol) were added. After three further cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in an oil bath at 100 hexane to 80% ethyl acetate) to give the title compound (1.01 g, 84%) as a solid.LRMS (m/z): 319/321 (M+1)+.1 H NMR (400 MHz, CHLOROFORM-d) delta ppm 7.21 (d, J=4.80 Hz, 1 H) 7.52 (s, 1 H) 7.63 (s, 1 H) 7.86 (s, 1 H) 8.53 (d, J=4.80 Hz, 1 H) 8.63 (s, 1 H)
With triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 20℃; for 4h;
According to Scheme 47, a solution of compound 73 (1.2 g, 6.25 mmol, Aldrich), compound 74 (1.2 g, 6.25 mmol, Aldrich), Et3N (0.9 mL, 6.25 mmol) in THF (10 mL) and DMF (3 mL) was stirred at room temperature for 4 h. After concentration, the residue was purified by column chromatography (40 g silica gel, 0-10% EtOAc/Hexane) to give compound 75 (615 mg, 1.8 mmol).
Step A: 4,6-dichloro-1 H-pyrrolor3,2-clpyridine: <strong>[25194-01-8]2,6-dichloro-4-nitro-pyridine</strong> (1 1 g, 57 mmol) was dissolved in dry tetrahydrofurane (300 ml_), cooled to -78C and treated dropwise with bromo(vinyl)magnesium (1 M in THF, 200 ml_, 200 mmol). The reaction was allowed to react at this temperature for 1 hour and then allowed to warm to -20C. The reaction mixture was then quenched with 200 ml of aqueous NH4CI and the mixture obtained was partitioned in ethyl acetate. The aqueous layer was extracted 3 times with 200 ml of ethyl acetate and the combined organic layer dried over Na2S04, filtered and concentrated in vacuo. Purification by Combi flash chromatography with a column of 120g and a gradient cyclohexane:0-100% ethyl acetate, and then with a column of 40 g and a gradient dichloromethane:0-10% ethyl acetate gave the title compound as brown solid (0.150 g, 1 .4%).
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 2h;
To a solution of <strong>[25194-01-8]2,6-dichloro-4-nitropyridine</strong> (0.1 g, 0.518 mmol) and benzyl amine (0.062 mL, 0.570 mmol) in 10 mL toluene was added cesium carbonate (0.253 g, 0.777 mmol). The mixture was degassed with nitrogen and 2,2'-bis(diphenylphosphino)-l,l'-binaphthalene (0.016 g, 0.026 mmol) and palladium acetate (5.82 mg, 0.026 mmol) were added. The mixture was heated at 100C for 2 hours, filtered through diatomaceous earth and concentrated. The residue was dissolved in ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, and concentrated. Recrystallization from 1 : 10 ethyl acetate-hexane afforded the title compound.
Benzyl alcohol (13.8 mL, 133 mmol) was added dropwise to a suspension of NaH (60% mineral oil suspension, 6.0 g, 150 mmol) in THF (250 mL), resulting in a slight exotherm. The mixture was stirred at room temperature for 30 minutes then cooled to 0 C. A solution of <strong>[25194-01-8]2,6-dichloro-4-nitropyridine</strong> (25 g, 129 mmol) in THF (125 mL) was added dropwise over 45 minutes. The reaction mixture was stirred at 0 C for an additional 30 minutes after the addition was complete. The reaction was quenched with H20 and the mixture was partitioned between H20 and EtOAc. The EtOAc layer was washed with H20 and brine. The organic layer was dried over MgS04 and filtered. The filtrate was concentrated under vacuum, then purified by dissolving the material in CH2Cl2/hexanes (1: 1) and filtering through a short plug of silica. Hexane trituration yielded 4-benzyloxy-2,6-dichlorpyridine (24.86 g, 75%) as an off-white solid. 1H NMR (acetone- d6): delta 5.35 (s, 2H), 7.16 (s, 2H), 7.39-7.49 (m, 3H), 7.53 (m, 2H).
75%
Step 1: 4-Benzyloxy-2,6-dichloropyridine Benzyl alcohol (13.8 mL, 133 mmol) was added dropwise to a suspension of NaH (60% mineral oil suspension, 6.0 g, 150 mmol) in THF (250 mL), resulting in a slight exotherm. The mixture was stirred at room temperature for 30 minutes before being cooled to 0 C. A solution of <strong>[25194-01-8]2,6-dichloro-4-nitropyridine</strong> (25 g, 129 mmol) in THF (125 mL) was added dropwise over 45 minutes. The reaction mixture was stirred at 0 C for an additional 30 minutes after the addition was complete. The reaction mixture was quenched with H20, and the mixture was partitioned between H20 and EtOAc. The EtOAc layer was washed withH20, and then brine. The organic layer was dried over MgS04and filtered. The filtrate was concentrated under vacuum. This was purified by dissolving the material in CH2Cl2/hexanes (1: 1) and filtering through a short plug of silica. Hexane trituration yielded 4-benzyloxy-2,6-dichlorpyridine (24.86 g, 75%) as an off-white solid. 1H NMR (acetone- d6): delta 5.35 (s, 2H), 7.16 (s, 2H), 7.39-7.49 (m, 3H), 7.53 (m, 2H)
With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 90℃; for 2h;Microwave irradiation;
Step 1: A mixture of <strong>[25194-01-8]2,6-dichloro-4-nitropyridine</strong> (1.0 equiv.), potassium carbonate (2 equiv.) and benzyl alcohol (2.4 equiv.) in NMP (4 M) were heated to 90 C. for 2 h in the microwave. The mixture was partitioned between water and EtOAc. The organic phase was washed with brine and dried over sodium sulfate. The solution was concentrated and dried under vacuo to give crude 4-(benzyloxy)-2,6-dichloropyridine and was used in the next step without further purification. LCMS (m/z) (M+H)=254.0/256.0, Rt=1.05 min.
3-(6-chloro-4-nitropyridin-2-yl)-2-(trifluoromethyl)imidazo[1,2-a]pyridine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
69%
With tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 100℃; for 0.5h;Microwave irradiation;
Step 1. A mixture of <strong>[25194-01-8]2,6-dichloro-4-nitropyridine</strong> (1.92 g, 10 mmol), 3- (tributylstannyl)-2-(trifluoromethyl)imidazo[l,2-a]pyridine (2 g, 4 mmol) and Pd(Ph3P)4 (230 mg, 0.02 mmol) was dissolved in dioxane (10 mL). The mixture was irradiated by microwave at 100 C for 30 minutes. The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography to give 3-(6-chloro-4-nitropyridin-2-yl)-2- (trifluoromethyl)imidazo[l,2-a]pyridine (0.8 g, 69%).
6-fluoro-3-(tributylstannyl)-2-(trifluoromethyl)imidazo[1,2-a]pyridine[ No CAS ]
[ 25194-01-8 ]
3-(6-chloro-4-nitropyridin-2-yl)-6-fluoro-2-(trifluoromethyl)imidazo[1,2-a]pyridine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
51%
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(eta3-allyl-mu-chloropalladium(II)); In 1,4-dioxane; at 100℃; for 0.333333h;Inert atmosphere;
Step 1. A mixture of 6-fluoro-3-(tributylstannyl)-2-(trifluoromethyl)imidazo[l,2- ajpyridine (1.68 g, 3.39 mmol), <strong>[25194-01-8]2,6-dichloro-4-nitropyridine</strong> (1.3 g, 6.78 mmol), APC (62 mg, 0.17 mmol), pentaphenyl(di-tert-butylphosphino)ferrocene (Q-Phos, 120 mg, 0.17 mmol) and dioxane (10 mL) was degassed by three cycles of vacuum pumping and N2 purging and heated at 100 C for 20 minutes until UPLC showed complete consumption of starting material. The reaction mixture was cooled and the solvent was evaporated. The residue was purified using silica gel column chromatography to afford 3-(6-chloro-4-nitropyridin-2-yl)-6- fluoro-2-(trifluoromethyl)imidazo[l,2-a]pyridine (620 mg, 51%) as a yellow solid. ]H NMR (DMSO-i delta 8.95 (ddd, J = 5.0, 2.5, 0.6 Hz, 1H), 8.49 (d, J = 1.6 Hz, 1H), 8.48 (d, J = 1.6 Hz, 1H), 7.98 (ddd, J = 10.1, 5.0, 0.6 Hz, 1H), 7.75 (ddd, J = 10.0, 8.0, 2.4 Hz, 1H)
(2,6-dichloropyridin-4-yl)(pyridin-1-ium-1-yl)amide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
98%
With potassium carbonate; In acetonitrile; at 23℃; for 4h;
General procedure: Potassium carbonate (9.0 mmol) for 3a-t or triethylamine (9.0 mmol) for 3u was added to a solution of 1-aminopyridinium iodide 1 (3.0 mmol) in acetonitrile (25 mL) for 3a-t or EtOH (25 mL) for 3u. The reaction mixtures were stirred vigorously for 10-20 min at room temperature to give a dark purple solution, to which electrophiles 2a-u (3.0 mmol) were added in one portion. The mixtures were stirred at rt for 3-24 h except for 3e, which was heated under reflux for 5h. Mixtures 3a-t were filtered to remove inorganic salts, which were washed with acetonitrile 3-5 times. The combined filtrates were concentrated in vacuo and the residues were purified either by gradient elution chromatography over silica gel and/or by recrystallization.
tert-butyl 5-(4,6-bis(benzyloxy)-5-((benzyloxy)carbonyl)-3-(((tert-butyldimethylsilyl)oxy)methyl)pyridin-2-yl)-4-(((tertbutyldimethylsilyl)oxy)methyl)indoline-1-carboxylate[ No CAS ]
tert-butyl 5-(4,6-bis(benzyloxy)-5-((benzyloxy)carbonyl)-3-(((tert-butyldimethylsilyl)oxy)methyl)pyridin-2-yl)-6-((2-(trimethylsilyl)ethoxy)methyl)indoline-1-carboxylate[ No CAS ]
benzyl 2,4-bis(benzyloxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-6-(2-formyl-1-methyl-6-((2-(trimethylsilyl)ethoxy)methyl)-1H-indol-5-yl)nicotinate[ No CAS ]
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