* 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.
Reference：
[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 3076 - 3080
2
[ 98-09-9 ]
[ 896722-50-2 ]
Yield
Reaction Conditions
Operation in experiment
80.7%
Stage #1: With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1 h; Stage #2: at 20℃; for 1 h;
(R)-6-Chloro-2-pyrrolidin-2-ylmethyl-1H-pyrrolo[2,3-b]pyridine. (Compound 45A) and (S)-6-Chloro-2-pyrrolidin-2-ylmethyl-1H-pyrrolo[2,3-b]pyridine. (Compound 45B); 6-Chloro-7-azaindole (9.3 g, 61.1 mmol), prepared as described (Synthesis, 1992), was dissolved in 100 ml anhydrous THF under N2. At 0° C., a 60percent dispersion of NaH 3.5 g (65.9 mmol) in mineral oil was added. After stirring for 1 hour at room temperature, the mixture was cooled (0° C.) and 8.7 ml (67.2 mmol) benzenesulfonyl chloride dissolved in 20 ml anhydrous THF was added. The reaction mixture was stirred at room temperature for 1 hour. Ethyl acetate was added to the mixture and the organic layer was washed three times with a saturated NaHCO3 solution, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by flash chromatography (diethyl ether/PE gradient (1:4 to pure diethyl ether) to give 1-benzenesulfonyl-6-chloro-1H-pyrrolo[2,3-b]pyridine (amorphous, 14.4 g, 80.7percent) (TLC diethyl ether/PE (1/1) Rf 0.37). LCMS; Rt: 1.98 min, ([M+H]+=293).
Stage #1: With sodium hydride In N,N-dimethyl-formamide; paraffin oil at 0 - 20℃; for 0.5 h; Stage #2: at 20℃; for 3 h;
To a solution of 6-chloro-1 H-pyrrolo[2,3-b]pyridine (1.37 g, 8.97 mmol) in DMF (1 00 ml),sodium hydride (60percent in paraffin, 1 g, 41 mmol) was added. The solution was stirred for30 min being allowed to warm up from 0 oc to rt. Subsequently, benzenesulfonic acidchloride (1.5 ml, 11.8 mmol) was added dropwise. The suspension was stirred 3 h atroom temperature and hydrolyzed with ice water. The resulting solid was filtered off under25 reduced pressure, washed thoroughly with water (75 ml) and finally with petroleum ether(15 ml). The resulting material was dried at 60 oc and purified by column chromatography (eluent: pure dichloromethane) yielding 856 mg of 1-(benzenesulfonyl)-6-chloropyrrolo[2,3-b]pyridine Xll-20a as a brownish solid.Yield: 32percent
Reference：
[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 3076 - 3080
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 1, p. 188 - 193
5
[ 271-63-6 ]
[ 896722-50-2 ]
Reference：
[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 3076 - 3080
6
[ 143468-07-9 ]
[ 896722-50-2 ]
Reference：
[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 3076 - 3080
7
[ 55052-24-9 ]
[ 896722-50-2 ]
Reference：
[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 3076 - 3080
8
[ 896722-50-2 ]
[ 5158-46-3 ]
[ 896722-51-3 ]
Yield
Reaction Conditions
Operation in experiment
88%
Stage #1: With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 40 h; Heating / reflux Stage #2: With water In tetrahydrofuran at 0℃;
A solution of methylzinc chloride in THF (2 M) (9 mL, 12 mmol) was added to 6-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.600 g, 2.05 mmol) and Pd(PPh3)4 (0.095 g, 0.08 mmol) in THF (30 mL). The mixture was refluxed for 40 h, cooled to 0° C., quenched with water and extracted with Et2O. The organic layer was concentrated and the residue was purified over a silica gel column eluting with EtOAc/hexane (1:5) to give N-protected 6-methyl-7-azaindole (0.495 g, 88percent).
Reference：
[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 3076 - 3080
[2] Patent: US2006/148801, 2006, A1, . Location in patent: Page/Page column 11
(R)-6-Chloro-2-pyrrolidin-2-ylmethyl-1H-pyrrolo[2,3-b]pyridine. (Compound 45A) and (S)-6-Chloro-2-pyrrolidin-2-ylmethyl-1H-pyrrolo[2,3-b]pyridine. (Compound 45B); 6-Chloro-7-azaindole (9.3 g, 61.1 mmol), prepared as described (Synthesis, 1992), was dissolved in 100 ml anhydrous THF under N2. At 0 C., a 60% dispersion of NaH 3.5 g (65.9 mmol) in mineral oil was added. After stirring for 1 hour at room temperature, the mixture was cooled (0 C.) and 8.7 ml (67.2 mmol) benzenesulfonyl chloride dissolved in 20 ml anhydrous THF was added. The reaction mixture was stirred at room temperature for 1 hour. Ethyl acetate was added to the mixture and the organic layer was washed three times with a saturated NaHCO3 solution, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by flash chromatography (diethyl ether/PE gradient (1:4 to pure diethyl ether) to give 1-benzenesulfonyl-6-chloro-1H-pyrrolo[2,3-b]pyridine (amorphous, 14.4 g, 80.7%) (TLC diethyl ether/PE (1/1) Rf 0.37). LCMS; Rt: 1.98 min, ([M+H]+=293).
A solution of methylzinc chloride in THF (2 M) (9 mL, 12 mmol) was added to <strong>[896722-50-2]6-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine</strong> (0.600 g, 2.05 mmol) and Pd(PPh3)4 (0.095 g, 0.08 mmol) in THF (30 mL). The mixture was refluxed for 40 h, cooled to 0 C., quenched with water and extracted with Et2O. The organic layer was concentrated and the residue was purified over a silica gel column eluting with EtOAc/hexane (1:5) to give N-protected 6-methyl-7-azaindole (0.495 g, 88%).
To a solution of 6-chloro-1H-pyrrolo[2,3-b]pyridine (1 .37 g, 8.97 mmol) in DMF (100 ml_), sodium hydride (60 % in paraffin, 1 g, 41 mmol) was added. The solution was stirred for 30 min being allowed to warm up from 0 C to rt. Subsequently, benzenesulfonic acid chloride (1 .5 mL, 1 1.8 mmol) was added dropwise. The suspension was stirred 3 h at room temperature and hydrolyzed with ice water. The resulting solid was filtered off under reduced pressure, washed thoroughly with water (75 mL) and finally with petroleum ether (15 mL). The resulting material was dried at 60 C and purified by column chromatography (eluent: pure dichloromethane) yielding 856 mg of 1 -(benzenesulfonyl)-6-chloro- pyrrolo[2,3-b]pyridine Xll-4a as a brownish solid. (1073) Yield: 32%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; at 20℃; for 8h;
To a solution of 7n (2.7 mmol, 410 mg), tetrabutylammonium hydrogen sulfate (3 mol%, 27 mg) and benzene sulfonyl chloride(3.3 mmol, 583 mg) in DCM (15 mL) placed at ice bath was added1N NaOH solutions (3.0 mL). The resulting mixture was stirred atroom temperature for 8 h. Water (30 mL) was added cautiously tothe reaction, and the mixture was extracted with DCM (15mL 3).The combined organic phase was washed with saturated NaCl (aq)for three times, dried over anhydride sodium sulfate and concentratedunder reduced vacuum. The crude product (14a) was directlyused in next step.
1-(benzenesulfonyl)-6-chloro-pyrrolo[2,3-b]pyridine-3-sulfonyl chloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
With chlorosulfonic acid; In acetonitrile; at 20℃; for 3h;
The obtained <strong>[896722-50-2]1-(benzenesulfonyl)-6-chloro-pyrrolo[2,3-b]pyridine</strong> Xll-20a (150 mg, 0.51mmol) was dissolved in acetonitrile (5 ml) and treated with chlorosulfonic acid (2 ml, 2.91mmol) dropwise. The mixture was refluxed for 3 h, cooled to room temperature,hydrolyzed with ice water (50 ml) and neutralized with a saturated solution of sodium10 hydrogen carbonate. The crude product was extracted with dichloromethane (3 times, 50ml each). The combined organic extracts were dried over MgS04, filtered andconcentrated. The resulting material was purified by column chromatography (eluent: puredichloromethane) yielding 163 mg of <strong>[896722-50-2]1-(benzenesulfonyl)-6-chloro-pyrrolo[2,3-b]pyridine</strong>-3-sulfonyl chloride Xll-20 as a yellowish solid.15 Yield: 81%1H NMR (600 MHz, CDCb) o: 8.48 (s, 1 H), 8.32 (d, J = 7.8 Hz, 2H), 8.18 (d, J = 8.3 Hz,1 H), 7.71 (t, J = 7.5 Hz, 1 H), 7.60 (t, J = 7.9 Hz, 2H), 7.41 (d, J = 8.4 Hz, 1 H).
81%
With chlorosulfonic acid; In acetonitrile; for 3h;Reflux;
The obtained 1 -(benzenesulfonyl)-6-chloro-pyrrolo[2,3-b]pyridine Xll-4a (150 mg, 0.51 mmol) was dissolved in acetonitrile (5 mL) and treated with chlorosulfonic acid (2 mL, 2.91 mmol) dropwise. The mixture was refluxed for 3 h, cooled to room temperature, hydrolyzed with ice water (50 mL) and neutralized with a saturated solution of sodium hydrogen carbonate. The crude product was extracted with dichloromethane (3 times, 50 mL each). The combined organic extracts were dried over MgS04, filtered and (1076) concentrated. The resulting material was purified by column chromatography (eluent: pure dichloromethane) yielding 163 mg of 1 -(benzenesulfonyl)-6-chloro-pyrrolo[2,3-b]pyridine- 3-sulfonyl chloride XII-4 as a yellowish solid. (1077) Yield: 81 % (1078) 1H NMR (600 MHz, CDCI3) d: 8.48 (s, 1 H), 8.32 (d, J = 7.8 Hz, 2H), 8.18 (d, J = 8.3 Hz, (1079) 1 H), 7.71 (t, J = 7.5 Hz, 1 H), 7.60 (t, J = 7.9 Hz, 2H), 7.41 (d, J = 8.4 Hz, 1 H).
To a solution of 6-chloro-1 H-pyrrolo[2,3-b]pyridine (1.37 g, 8.97 mmol) in DMF (1 00 ml),sodium hydride (60% in paraffin, 1 g, 41 mmol) was added. The solution was stirred for30 min being allowed to warm up from 0 oc to rt. Subsequently, benzenesulfonic acidchloride (1.5 ml, 11.8 mmol) was added dropwise. The suspension was stirred 3 h atroom temperature and hydrolyzed with ice water. The resulting solid was filtered off under25 reduced pressure, washed thoroughly with water (75 ml) and finally with petroleum ether(15 ml). The resulting material was dried at 60 oc and purified by column chromatography (eluent: pure dichloromethane) yielding 856 mg of 1-(benzenesulfonyl)-6-chloropyrrolo[2,3-b]pyridine Xll-20a as a brownish solid.Yield: 32%
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