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[ CAS No. 5330-63-2 ]

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Chemical Structure| 5330-63-2
Chemical Structure| 5330-63-2
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CAS No. :5330-63-2 MDL No. :MFCD07127698
Formula : C11H14ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :227.69 g/mol Pubchem ID :-
Synonyms :

Safety of [ 5330-63-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5330-63-2 ]

  • Downstream synthetic route of [ 5330-63-2 ]

[ 5330-63-2 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 2831-66-5 ]
  • [ 5330-63-2 ]
  • [ 652153-34-9 ]
YieldReaction ConditionsOperation in experiment
52% Stage #1: t-butyl 3-chlorophenylcarbamate With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: 2,4-dichloro-1,3,5-triazine In tetrahydrofuran at 20℃;
52% Stage #1: t-butyl 3-chlorophenylcarbamate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: 2,4-dichloro-1,3,5-triazine In tetrahydrofuran at 0 - 20℃; 1 Example 1; 3- ( (5- (4- ( (3-chlorophenyl) amino) -1,3, 5-triazin-2-yl) - 3-pyridinyl) [AMINO)-1-PROPANOL] (Compound 1) 3-Chloroaniline (29.4 g, 229 mmol) was dissolved in THF (250 mL) at [20 °C.] A THF solution (80 mL) of Boc2O (50 g, 229 mmol) was added slowly to the mixture of 3-chloroaniline and THF. The resulting mixture was stirred for 3 days and then concentrated. The crude product was purified by recrystallization from EtOAc/Hexane three times to give Compound 1A (40.4 g, 78%) as a white [SOLID. IH] NMR (300 MHz, [CDCL3)] [5] 7.52 (s, 1H), 7.17 [(M,] 2H), 7.00 (dt, J= 7.4, 1.8 Hz, 1H), 6.49 (s, 1H), 1.52 (s, 9H); MS (ES) [M/Z] : 250 (M+Na). Anal. Calcd. For [CLLHL4NO2CL] : C, 58.03 ; H, 6. 20 ; N, 6.15. Found: C, 58. 14; H, 6.22 ; N, 6.10. THF (150 mL) was added to a mixture of Compound [1A] (5.5 g, 24.2 mmol) and NaH (60% in mineral oil, 2.4 g, 60.6 mmol) at 0 [°C] under N2. The mixture was stirred at [20 °C] for 1 h and then cooled to [0 °C] and Compound 1B (6.2 g, 41.2 mmol; prepared as described in Harris, R. L. N. Synthesis 1981,907) was added. After the mixture was stirred at [20 °C] overnight, the solvent was evaporated and the residue was purified by flash chromatography (10% EtOAc in hexanes) to give Compound 1C (4.3 g, 52%) as a white solids NMR (300 MHz, [CDC13)] 8 8.72 (s, 1H), 7.40 (m, 2H), 7.22 (brs, 1H), 7.11 [(M,] [1H),] 1.48 (s, 9H); MS (ES) m/z: 363 (M+Na). Anal. Calcd. For [C14HL4N402CL2] : C, 49.28 ; H, 4.14 ; N, 16.42. Found: C, 49. 52 ; H, 4.13 ; N, 16.41. A mixture of 5-bromonicotinic acid Compound 1D (10 g, 49.5 mmol), [T-BUOH] (100 [ML),] triethylamine (15.2 g, [150] mmol) and DPPA (20.4 g, 74 mmol) in toluene (100 mL) was stirred at [65 °C] for 40 min and then warmed to [100 °C FOR] 22 h under nitrogen. The mixture was cooled and concentrated under vacuum. The crude product was purified by column chromatography on [SI02] eluting with ethyl acetate/hexane to give Compound [1E] (10.52 g, 78%) as a white [SOLID. LH NMR (300 MHZ, CDCL3) 6 8.] 32 (m, 3H), 6.97 (brs, 1H), 1.53 (s, 9H); MS (ES) [M/Z] : 273,275 [(M+H+).] Anal. Calcd. For [CLOHI3N202BR] : C, 43.98 ; H, 4.80 ; N, 10.26. Found: C, 43. 88 ; H, 4.52 ; N, 10.20. A mixture of Compound [1E] (2.85 g, 10.44 mmol), (3-bromopropoxy)-t- butyldimethylsilane (3.96 g, 15.66 mmol) and [CS2CO3] (10.21 g, 31.3 mmol) in anhydrous DMF (55 mL) was stirred at 70 [°C] for 23 h under nitrogen. The mixture was cooled, diluted with water and extracted with ether (3x). The organic phase was dried [(NA2S04)] and concentrated. The product was purified by column chromatography (eluting with EtOAc/hexane) to give Compound IF (4.2 g, 90%) as a yellow [OIL. 1H] NMR (300 MHz, [CDCL3)] [8] 8.45 (brs, 2H), 7.77 (brs, 1H), 3.73 (brt, J= 7.3 Hz, 2H), 3.62 (t, J= 5.9 Hz, 2H), 1.81 [(M,] 2H), 1.45 (s, 9H), 0.84 (s, 9H), 0.00 (s, 6H); MS (ES) m/z: 445,447 [(M+H+).] Anal. Calcd. For [CLGH33N203BRSI] : C, 51.23 ; H, 7.47 ; N, 6.29. Found: C, 51.45 ; H, 7.47 ; N, 6.53. [N-BULI] (2.3 [ML,] 2.5 M, 5.65 mmol) was added dropwise to a solution of Compound IF (1.26 g, 2.82 mmol) in anhydrous THF (10 mL) at-78 °C and the mixture was stirred for 20 min. Anhydrous zinc chloride (8.47 mL, 1 M in ether, 8.47 mmol) was added dropwise to the THF solution containing Compound IF at-78 [°C] and stirred for 10 min before it was warmed to [20 °C] by removing the dry-ice bath. A mixture of Compound 1C (640 mg, 1.88 mmol) and [PD (PPH3)] 4 (109 [MG,] 0.094 mmol) in dry THF (8 mL) was added. The resulting mixture was stirred at 20 [°C] for 10 min, then at 70 [°C] for 22 h and the solvent was removed under vacuum. The residue was partitioned between water and ether and then separated. The aqueous layer was extracted with ether (3x). The combined organic layers were dried [(NA2SO4)] and concentrated. The product (a mixture of bis-Boc-and mono-Boc-protected coupling products) was purified by column chromatography to give 458 mg of yellow foam. The yellow foam was mixed with TFA (5 mL) and the mixture was stirred at [20 °C] for 2 h and then concentrated. NH40H was added, followed by water addition until the pH of the aqueous layer reached about 10-11. A yellow solid was formed, collected through filtration and then dried under vacuum. The product was purified by column chromatography to give Compound 1 (208 mg, 73%) as a yellow [SOLID. 1H] NMR (300 MHz, DMSO-d6) 6 10.55 (s, [1H),] 8.89 (s, [1H),] 8.18 (brs, [1H),] 8.06 (s, [1H),] 7.76 (s, 1H), 7.71 (d, [J=] 8.0 Hz, 1H), 7.41 (t, [J= 8. 0 HZ, 1H),] 7.15 (d, [V= 7. 9 HZ, 1H),] 6.19 (brs, 1H), 4.54 (t, [J= 5. 0 HZ,] 1H), 3.55 [(M,] 2H), 3.18 [(M,] 2H), 1.80 [(M,] 2H); MS (ES) [M/Z] : 357 [(M+H+).] Anal. Calcd. For C17H17N6OCl30. 35 [H20] : C, 56.23 ; H, 4.91 ; N, 23.14. Found: C, 56.63 ; H, 4.78 ; N, 22.76.
  • 2
  • [ 24424-99-5 ]
  • [ 108-42-9 ]
  • [ 5330-63-2 ]
YieldReaction ConditionsOperation in experiment
100% In methanol at 100℃; for 6h;
100% Stage #1: 3-chloro-aniline With triethylamine In tetrahydrofuran; water at 20℃; for 0.0833333h; Stage #2: di-<i>tert</i>-butyl dicarbonate In tetrahydrofuran; water at 0 - 20℃; for 6h;
97% With 1,1'-hexane-1,6-diylbis(3-methylpyridinium)tetrachlorocobaltate(II) In neat (no solvent) at 20℃; for 1h;
96% With poly(4-vinylpyridine) at 20℃; for 0.783333h;
96% With 1,4-disulfopiperazine-1,4-diium chloride In neat (no solvent) at 20℃; for 0.5h; Green chemistry; chemoselective reaction;
95% With guanidine hydrochloride In ethanol at 35 - 40℃; for 1h; 2.1. General procedure for N-tert-butoxycarbonylation of amines: General procedure: Amine (1 mmol) was added to a magnetically stirred solution of guanidine hydrochloride (15 mol%) and di-tert-butyl dicarbonate (1.2 mmol) in EtOH (1 mL), at 35-40°C and stirred for appropriate time (Table 1). After completion of the reaction (followed by TLC or GC), EtOH was evaporated under vacuum and the residue either was washed with water to remove the catalyst or was dissolved in CH2Cl2 (or EtOAc) and filtered off to separate out the catalyst. Evaporation of the organic solvent (if used in work up) gives almost a pure product. In the cases of using an excess (Boc)2O the product was washed with petroleum ether or hexane to recover the residual (Boc)2O. If necessary, the product was further purified either by crystallization (hexane and dichloromethane, or diethyl ether and petroleum ether) or silica gel column chromatography using EtOAc-hexane (1: 6) as eluent.
95% In PEG-400 at 20℃; for 0.166667h;
94% With sulfonic acid-functionalized ordered nanoporous Na+-montmorillonite at 20℃; for 1.05h; Neat (no solvent);
94% With succinimide-N-sulfonic acid at 20℃; for 0.533333h; Neat (no solvent);
94% With γ-Fe2O3@SiO2 nanoparticles at 20℃; for 0.5h; chemoselective reaction;
94% With iron(III) trifluoromethanesulfonate In neat (no solvent) at 20℃; for 0.133333h; Green chemistry; N-Boc protection of amines General procedure: Fe(OTf)3 (1 mol%) was added to a magnetically stirred mixture of anamine (1 mmol) and Boc2O (1 mmol) at room temperature. The mixturewas stirred until completion of the reaction (TLC), then diluted withEtOAc and washed with water. The organic layer was dried overanhydrous MgSO4, then the solvent was distillated off under vacuum toyield the highly pure N-Boc derivatives
93% In water at 25 - 28℃; for 0.25h; ultrasound;
93% With thioglycoluril In ethanol at 30 - 40℃; for 0.5h; chemoselective reaction;
93% In ethyl acetate at 20℃; for 13h;
93% With succinimidinium N-sulfonic acid hydrogen sulfate In neat (no solvent) at 20℃; for 0.116667h; Green chemistry;
92% With rice-husk-supported FeCl3 nano particles In neat (no solvent) at 20℃; for 0.416667h;
92% With choline chloride; urea at 50℃; Green chemistry; General procedure General procedure: A dried test tube, equipped with a magnetic stir bar, wascharged with 0.5 cm3 DES, amine derivatives(0.5 mmol), and Boc2O (0.5 mmol) and the mixture washeated at 50 C until the reaction was complete (monitoredby TLC and IR). After this time, 5 cm3 water wasadded and in the most cases a white solid was obtained.The solid product was collected by filtration and washedsuccessively with water and recrystallized from ethanolto get the pure final product [51-60]. The viscousproducts extracted with ethyl acetate and were purifiedby column chromatography, using ethyl acetate-petroleumether.
90% In neat (no solvent) at 100℃; for 0.0666667h; Microwave irradiation; Green chemistry; chemoselective reaction; (General procedure for the N-tert-butoxycarbonylation of amines: General procedure: Amine (1 mmol) and di-tert-butyl dicarbonate [(Boc)2O] (1.1 mmol) were placed in a microwave reaction vial. The LG microwave oven MG 555f was programmed to 300 W at 100 °C. The reaction was monitored using TLC. After the reaction, ice water was added to the reaction mixture which resulted in the precipitation of the product. The solid product was merely filtered off and washed with excess cold water. The product was pure enough for all practical purposes. For characterization purpose, it was further purified by column chromatography (Neutral Alumina as adsorbent, solvent system: Hexane: Ethyl acetate (7.5:2.5)).
89% With 1,3-disulfonic acid imidazolium hydrogen sulfate In neat (no solvent) at 20℃; for 0.25h; Green chemistry; chemoselective reaction; 2.4 General procedure for the N-Boc protection of amines General procedure: Amine (1 mmol) was added to the mixture of (Boc)2O (1 mmol) and DSIMHS (6.5 mg, ~ 0.02 mmol) with constant stirring at room temperature under solvent-free conditions. After completion of the reaction (monitored by TLC), ethyl acetate (3 × 5 mL) was added to the reaction mixture and the catalyst was decanted and washed with ethyl acetate (2 × 5 mL) and dried. The product was purified by column chromatography, using ethyl acetate-petroleum ether (2:8) eluent.
89% With N-sulfonic acid poly(4-vinyl)pyridinium chloride In neat (no solvent) at 20℃; for 0.833333h;
80% at 30 - 33℃; for 1h;
78% In tetrahydrofuran at 20℃; for 72h;
78% In tetrahydrofuran at 20℃; for 72h; 1 Example 1; 3- ( (5- (4- ( (3-chlorophenyl) amino) -1,3, 5-triazin-2-yl) - 3-pyridinyl) [AMINO)-1-PROPANOL] (Compound 1) 3-Chloroaniline (29.4 g, 229 mmol) was dissolved in THF (250 mL) at [20 °C.] A THF solution (80 mL) of Boc2O (50 g, 229 mmol) was added slowly to the mixture of 3-chloroaniline and THF. The resulting mixture was stirred for 3 days and then concentrated. The crude product was purified by recrystallization from EtOAc/Hexane three times to give Compound 1A (40.4 g, 78%) as a white [SOLID. IH] NMR (300 MHz, [CDCL3)] [5] 7.52 (s, 1H), 7.17 [(M,] 2H), 7.00 (dt, J= 7.4, 1.8 Hz, 1H), 6.49 (s, 1H), 1.52 (s, 9H); MS (ES) [M/Z] : 250 (M+Na). Anal. Calcd. For [CLLHL4NO2CL] : C, 58.03 ; H, 6. 20 ; N, 6.15. Found: C, 58. 14; H, 6.22 ; N, 6.10. THF (150 mL) was added to a mixture of Compound [1A] (5.5 g, 24.2 mmol) and NaH (60% in mineral oil, 2.4 g, 60.6 mmol) at 0 [°C] under N2. The mixture was stirred at [20 °C] for 1 h and then cooled to [0 °C] and Compound 1B (6.2 g, 41.2 mmol; prepared as described in Harris, R. L. N. Synthesis 1981,907) was added. After the mixture was stirred at [20 °C] overnight, the solvent was evaporated and the residue was purified by flash chromatography (10% EtOAc in hexanes) to give Compound 1C (4.3 g, 52%) as a white solids NMR (300 MHz, [CDC13)] 8 8.72 (s, 1H), 7.40 (m, 2H), 7.22 (brs, 1H), 7.11 [(M,] [1H),] 1.48 (s, 9H); MS (ES) m/z: 363 (M+Na). Anal. Calcd. For [C14HL4N402CL2] : C, 49.28 ; H, 4.14 ; N, 16.42. Found: C, 49. 52 ; H, 4.13 ; N, 16.41. A mixture of 5-bromonicotinic acid Compound 1D (10 g, 49.5 mmol), [T-BUOH] (100 [ML),] triethylamine (15.2 g, [150] mmol) and DPPA (20.4 g, 74 mmol) in toluene (100 mL) was stirred at [65 °C] for 40 min and then warmed to [100 °C FOR] 22 h under nitrogen. The mixture was cooled and concentrated under vacuum. The crude product was purified by column chromatography on [SI02] eluting with ethyl acetate/hexane to give Compound [1E] (10.52 g, 78%) as a white [SOLID. LH NMR (300 MHZ, CDCL3) 6 8.] 32 (m, 3H), 6.97 (brs, 1H), 1.53 (s, 9H); MS (ES) [M/Z] : 273,275 [(M+H+).] Anal. Calcd. For [CLOHI3N202BR] : C, 43.98 ; H, 4.80 ; N, 10.26. Found: C, 43. 88 ; H, 4.52 ; N, 10.20. A mixture of Compound [1E] (2.85 g, 10.44 mmol), (3-bromopropoxy)-t- butyldimethylsilane (3.96 g, 15.66 mmol) and [CS2CO3] (10.21 g, 31.3 mmol) in anhydrous DMF (55 mL) was stirred at 70 [°C] for 23 h under nitrogen. The mixture was cooled, diluted with water and extracted with ether (3x). The organic phase was dried [(NA2S04)] and concentrated. The product was purified by column chromatography (eluting with EtOAc/hexane) to give Compound IF (4.2 g, 90%) as a yellow [OIL. 1H] NMR (300 MHz, [CDCL3)] [8] 8.45 (brs, 2H), 7.77 (brs, 1H), 3.73 (brt, J= 7.3 Hz, 2H), 3.62 (t, J= 5.9 Hz, 2H), 1.81 [(M,] 2H), 1.45 (s, 9H), 0.84 (s, 9H), 0.00 (s, 6H); MS (ES) m/z: 445,447 [(M+H+).] Anal. Calcd. For [CLGH33N203BRSI] : C, 51.23 ; H, 7.47 ; N, 6.29. Found: C, 51.45 ; H, 7.47 ; N, 6.53. [N-BULI] (2.3 [ML,] 2.5 M, 5.65 mmol) was added dropwise to a solution of Compound IF (1.26 g, 2.82 mmol) in anhydrous THF (10 mL) at-78 °C and the mixture was stirred for 20 min. Anhydrous zinc chloride (8.47 mL, 1 M in ether, 8.47 mmol) was added dropwise to the THF solution containing Compound IF at-78 [°C] and stirred for 10 min before it was warmed to [20 °C] by removing the dry-ice bath. A mixture of Compound 1C (640 mg, 1.88 mmol) and [PD (PPH3)] 4 (109 [MG,] 0.094 mmol) in dry THF (8 mL) was added. The resulting mixture was stirred at 20 [°C] for 10 min, then at 70 [°C] for 22 h and the solvent was removed under vacuum. The residue was partitioned between water and ether and then separated. The aqueous layer was extracted with ether (3x). The combined organic layers were dried [(NA2SO4)] and concentrated. The product (a mixture of bis-Boc-and mono-Boc-protected coupling products) was purified by column chromatography to give 458 mg of yellow foam. The yellow foam was mixed with TFA (5 mL) and the mixture was stirred at [20 °C] for 2 h and then concentrated. NH40H was added, followed by water addition until the pH of the aqueous layer reached about 10-11. A yellow solid was formed, collected through filtration and then dried under vacuum. The product was purified by column chromatography to give Compound 1 (208 mg, 73%) as a yellow [SOLID. 1H] NMR (300 MHz, DMSO-d6) 6 10.55 (s, [1H),] 8.89 (s, [1H),] 8.18 (brs, [1H),] 8.06 (s, [1H),] 7.76 (s, 1H), 7.71 (d, [J=] 8.0 Hz, 1H), 7.41 (t, [J= 8. 0 HZ, 1H),] 7.15 (d, [V= 7. 9 HZ, 1H),] 6.19 (brs, 1H), 4.54 (t, [J= 5. 0 HZ,] 1H), 3.55 [(M,] 2H), 3.18 [(M,] 2H), 1.80 [(M,] 2H); MS (ES) [M/Z] : 357 [(M+H+).] Anal. Calcd. For C17H17N6OCl30. 35 [H20] : C, 56.23 ; H, 4.91 ; N, 23.14. Found: C, 56.63 ; H, 4.78 ; N, 22.76.
70% With aminosulfonic acid at 40℃; for 2h; Sonication; Procedure for a 1st protection of 3-chloroaniline 19.5 mmol of 3-chloroaniline were combined with 21.5 mmol of Boc anhydride and 20 mmol of sulfamic acid. Sonicated the resultant mixture at 40 °C using a commercially available 40 kHz ultrasonic cleaner for 2 hours. Filtered out sulfamic acid salts using diethyl ether for transfer. Worked up with sodium bicarbonate. Product recrystallized from diethyl ether to afford tert-butyl (3-chlorophenyl)carbamate in 70% yield. Rf=0.15(prod.) in 1:20 EtOAc:hexanes.
39% With triethylamine In tetrahydrofuran at 25 - 40℃; for 28h; Inert atmosphere; 1-4 Production Example 1-4:
Synthesis of m-chloro-N-t-butoxycarbonylaniline 2.0 g (15.7 mmol) of m-chloroaniline, 1.8 g (17.3 mmol) of triethylamine, and 10 mL of THF were placed in a 100-mL test tube purged with nitrogen. While stirring the mixture, 3.4 g (15.7 mmol) of di-t-butyl dicarbonate/10 mL of THF solution was added dropwise. The resulting mixture was stirred at 25° C. for 4 hours, and then further stirred at 40° C. for 24 hours. After the obtained reaction mixture was cooled to 25° C., the solvent was distilled off. Then, 20 mL of toluene was added to the obtained concentrated residue, and the resulting mixture was washed once with 20 mL of 1 M citric acid aqueous solution and once with 20 mL of water. The obtained organic phase was dried over magnesium sulfate, and then dried under reduced pressure, thereby obtaining 1.4 g of a compound represented by the above formula (m-chloro-N-t-butoxycarbonylaniline) (yield: 39%). The 1H-NMR analysis results of the compound represented by the above formula are shown below. 1H-NMR (CDCl3) δ (ppm)=7.52 (s, 1H), 7.21-7.14 (m, 2H), 7.00 (dt, J=7.5, 1.7 Hz, 1H), 6.52 (s, 1H), 1.52 (s, 9H)
39% With triethylamine In tetrahydrofuran at 25 - 40℃; for 28h; Inert atmosphere; 2-4 Production Example 2-4: Synthesis of m-chloro-N-t-butoxycarbonylaniline 2.0 g (15.7 mmol) of m-chloroaniline, 1.8 g (17.3 mmol) of triethylamine, and 10 mL of THF were placed in a 100-mL test tube purged with nitrogen. While stirring the mixture, 3.4 g (15.7 mmol) of di-t-butyl dicarbonate/10 mL of THF solution was added dropwise. The obtained mixture was stirred at 25° C. for 4 hours, and then further stirred at 40° C. for 24 hours. After the obtained reaction mixture was cooled to 25° C., the solvent was distilled off. Then, 20 mL of toluene was added to the obtained concentrated residue, and the resulting mixture was washed once with 20 mL of 1 M citric acid aqueous solution and once with 20 mL of water. The obtained organic phase was dried over magnesium sulfate, and then dried under reduced pressure, thereby obtaining 1.4 g of a compound represented by the above formula (m-chloro-N-t-butoxycarbonylaniline) (yield: 39%). The 1H-NMR analysis results of the compound represented by the above formula are shown below. 1H-NMR (CDCl3) δ (ppm)=7.52 (s, 1H), 7.21-7.14 (m, 2H), 7.00 (dt, J=7.5, 1.7 Hz, 1H), 6.52 (s, 1H), 1.52 (s, 9H)
In ethanol at 20℃;
In tetrahydrofuran
In water at 20℃;

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[23]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2004/9562, 2004, A1 Location in patent: Page 31-33
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[25]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - US2020/24237, 2020, A1 Location in patent: Paragraph 0129-0131
[26]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - US10689478, 2020, B2 Location in patent: Page/Page column 124
[27]Wang, Peng; Farmer, Marcus E.; Huo, Xing; Jain, Pankaj; Shen, Peng-Xiang; Ishoey, Mette; Bradner, James E.; Wisniewski, Steven R.; Eastgate, Martin D.; Yu, Jin-Quan [Journal of the American Chemical Society, 2016, vol. 138, # 29, p. 9269 - 9276]
[28]Xiong, Xiaodong; Yeung, Ying-Yeung [Angewandte Chemie - International Edition, 2016, vol. 55, # 52, p. 16101 - 16105][Angew. Chem., 2016, vol. 128, # 52, p. 16335 - 16339,5]
[29]Jiang, Xipeng; Jiang, Yaqiqi; Liu, Qianqian; Li, Bao; Shi, Da-Qing; Zhao, Yingsheng [Journal of Organic Chemistry, 2022, vol. 87, # 5, p. 3546 - 3554]
  • 3
  • N,N-di-(tert-butoxycarbonyl)-3-chloroaniline [ No CAS ]
  • [ 5330-63-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In methanol Heating;
  • 4
  • [ 108-42-9 ]
  • [ 5330-63-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: DMAP / tetrahydrofuran / Heating 2: K2CO3 / methanol / Heating
  • 5
  • [ 5330-63-2 ]
  • 3-((4-(4-((3-chlorophenyl)amino)-1,3,5-triazin-2-yl)-2-pyridinyl)amino)-1-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: NaH / tetrahydrofuran / 1 h / 20 °C 1.2: 52 percent / tetrahydrofuran / 20 °C 2.1: bis(trimethyltin); tetrakis(triphenylphosphine)palladium; LiCl / 2,6-di-tert-butyl-4-methylphenol / dioxane / 1.5 h / 90 °C 2.2: tris(dibenzylideneacetone)dipalladium-chloroform; AsPh3; 2,6-di-tert-butyl-4-methylphenol / toluene / 3.5 h / 100 °C 3.1: 750 mg / CF3CO2H / CH2Cl2 / 2 h / 20 °C
  • 6
  • [ 5330-63-2 ]
  • 3-((5-(4-((3-chlorophenyl)amino)-1,3,5-triazin-2-yl)-3-pyridinyl)amino)-1-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaH / tetrahydrofuran / 1 h / 20 °C 1.2: 52 percent / tetrahydrofuran / 20 °C
  • 7
  • [ 5330-63-2 ]
  • 3-((6-(4-((3-chlorophenyl)amino)-1,3,5-triazin-2-yl)pyrazin-2-yl)amino)-1-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: NaH / tetrahydrofuran / 1 h / 20 °C 1.2: 52 percent / tetrahydrofuran / 20 °C 2.1: bis(trimethyltin); tetrakis(triphenylphosphine)palladium; LiCl / 2,6-di-tert-butyl-4-methylphenol / dioxane / 4 h / Heating 2.2: dichlorobis(triphenylphosphine)palladium; LiCl / toluene / 100 °C 3.1: 1.5 mg / CF3CO2H / CH2Cl2 / 4 h / 20 °C
  • 8
  • [ 5330-63-2 ]
  • [ 652153-43-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaH / tetrahydrofuran / 1 h / 20 °C 1.2: 52 percent / tetrahydrofuran / 20 °C 2.1: bis(trimethyltin); tetrakis(triphenylphosphine)palladium; LiCl / 2,6-di-tert-butyl-4-methylphenol / dioxane / 1.5 h / 90 °C 2.2: tris(dibenzylideneacetone)dipalladium-chloroform; AsPh3; 2,6-di-tert-butyl-4-methylphenol / toluene / 3.5 h / 100 °C
  • 9
  • [ 5330-63-2 ]
  • [4-(6-{<i>tert</i>-butoxycarbonyl-[3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-propyl]-amino}-pyrazin-2-yl)-[1,3,5]triazin-2-yl]-(3-chloro-phenyl)-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaH / tetrahydrofuran / 1 h / 20 °C 1.2: 52 percent / tetrahydrofuran / 20 °C 2.1: bis(trimethyltin); tetrakis(triphenylphosphine)palladium; LiCl / 2,6-di-tert-butyl-4-methylphenol / dioxane / 4 h / Heating 2.2: dichlorobis(triphenylphosphine)palladium; LiCl / toluene / 100 °C
  • 10
  • [ 1239374-13-0 ]
  • [ 5330-63-2 ]
YieldReaction ConditionsOperation in experiment
73% With methanol; tris(propionitrile)tricarbonylmolybdenum(0) at 130℃; for 0.25h; Microwave irradiation; Inert atmosphere; chemoselective reaction;
  • 11
  • [ 5330-63-2 ]
  • [ 3422-01-3 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: t-butyl 3-chlorophenylcarbamate With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 0℃; for 0.5h; Stage #2: With iodine In tetrahydrofuran at -78 - 0℃; for 1h;
  • 12
  • [ 5330-63-2 ]
  • [ 1287791-62-1 ]
  • [ 1287791-61-0 ]
YieldReaction ConditionsOperation in experiment
1: 18% 2: 38% Stage #1: t-butyl 3-chlorophenylcarbamate With tert.-butyl lithium In tetrahydrofuran; pentane at -78 - -20℃; for 1h; Stage #2: With iodine In tetrahydrofuran; pentane at -78 - -20℃; for 1h;
  • 13
  • [ 5330-63-2 ]
  • [ 1384312-84-8 ]
YieldReaction ConditionsOperation in experiment
80% With water-d2 In tetrahydrofuran at 40℃; for 18h;
  • 14
  • [ 5330-63-2 ]
  • [ 1384313-08-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydride / diethyl ether / 20 °C / Inert atmosphere 2: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; 4,4'-di-tert-butyl-2,2'-bipyridine / tert-butyl methyl ether / 17 h / 50 °C / Inert atmosphere
  • 15
  • [ 5330-63-2 ]
  • [ 1384313-14-7 ]
  • [ 1384313-16-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: water-d2 / tetrahydrofuran / 18 h / 40 °C 2: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; 4,4'-di-tert-butyl-2,2'-bipyridine / tert-butyl methyl ether / 13 h / 50 °C / Inert atmosphere
  • 16
  • [ 5330-63-2 ]
  • [ 73183-34-3 ]
  • [ 1186637-28-4 ]
  • [ 1384312-60-0 ]
YieldReaction ConditionsOperation in experiment
1: 25% 2: 50% With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; 4,4'-di-tert-butyl-2,2'-bipyridine In tert-butyl methyl ether at 50℃; for 20h; Inert atmosphere; regioselective reaction;
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