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Chemical Structure| 479633-63-1
Chemical Structure| 479633-63-1
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Product Details of [ 479633-63-1 ]

CAS No. :479633-63-1 MDL No. :MFCD09907939
Formula : C13H10ClN3O2S Boiling Point : -
Linear Structure Formula :- InChI Key :BTOJSYRZQZOMOK-UHFFFAOYSA-N
M.W : 307.76 Pubchem ID :44228967
Synonyms :

Calculated chemistry of [ 479633-63-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.08
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 76.57
TPSA : 73.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.44
Log Po/w (XLOGP3) : 3.17
Log Po/w (WLOGP) : 3.71
Log Po/w (MLOGP) : 2.93
Log Po/w (SILICOS-IT) : 1.86
Consensus Log Po/w : 2.82

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.17
Solubility : 0.0209 mg/ml ; 0.0000679 mol/l
Class : Moderately soluble
Log S (Ali) : -4.38
Solubility : 0.0129 mg/ml ; 0.0000418 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.14
Solubility : 0.00221 mg/ml ; 0.00000718 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.58

Safety of [ 479633-63-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 479633-63-1 ]

* 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.

  • Upstream synthesis route of [ 479633-63-1 ]
  • Downstream synthetic route of [ 479633-63-1 ]

[ 479633-63-1 ] Synthesis Path-Upstream   1~8

  • 1
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YieldReaction ConditionsOperation in experiment
85%
Stage #1: With sodium hydride In tetrahydrofuran at 20℃; for 0.583333 h;
Stage #2: at 20℃; for 1 h;
Example 1; Preparation of Thiazolyl-Pyrrolo[2,3-</]Pyrimidines of the Invention; [0221] 4-Chloro-7-(toluene-4-sulfonyl)-7H-pyrroIo[2,3-*/]pyrimidine; To a solution of (10 g, 65.1 mmol] of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine in 25OmL of dry THF was cautiously added portionwise over 5 minutes time [2.86 g, 71.6 mmol] <n="63"/>sodium hydride (60percent oil dispersion). Reaction was then allowed to stir for 30 minutes at ambient temperature under a blanket of nitrogen gas. [12.96 g, 68.0 mmol] of solid toluene sulphonyl chloride was then added, in one portion and the reaction mixture was allowed to stir for one hour additional at ambient temperature. Ten mL of water was then cautiously added to the reaction (a quench for the excess hydride) and the solvent was removed under reduced pressure to 1/4 the original volume. The residue was then suspended in 300 mL of water, stirred at ambient temperature for 30 minutes and isolated as a white solid via suction filtration. The material was washed with additional water and the damp cake was suspended in a minimum of acetonitrile and stirred overnight at ambient temperature. The precipitate was isolated via suction filtration and washed cautiously with cold acetonitrile and washed with hexanes; material air dried. Yield: 17.2g of an off white solid (85percent). [0222 ] NMR: 500MHz in CDCL3 δ8.75(s,lH), 8.09(d,2H J=8.5Hz),7.78(d,lH J= 4.1Hz), 7.36(d,2H J=8.5Hz), 6.70(d,lH J= 4.1Hz), 2.4(s,3H)
Reference: [1] Patent: WO2007/117494, 2007, A1, . Location in patent: Page/Page column 61-62
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YieldReaction ConditionsOperation in experiment
97% With sodium hydroxide In water; acetone at 0 - 20℃; for 6 h; EXAMPLE 13-((3Λ,4Λ)-4-Methyl-3-(methyl(7H-pyrrolo[2,3-rf]pyrimidin-4- yl)amino)piperidin-l-yl)-3-oxopropanenitrile mono citrate salt (CP-690550 citrate salt)Step 1[00151] 4-Chloro-7-tosyl-7H-pyrrolor2,3-6πpynmidine: At about O 0C, sodium hydroxide (2 mol/L in water, 8 mL, 1.20 equiv.) was added to a solution of 4- methylbenzene-1-sulfonyl chloride (2.7 g, 13.9 mmol, 1.10 equiv.) and 4-chloro- 7H-pyrrolo[2,3-J]pyrimidine (2 g, 12.8 mmol, 1.00 equiv.) in acetone (20 mL). The resulting solution was stirred at about 20 0C for about 6 hours. The solids were collected by filtration and washed with acetone/water to give the title product as a white solid (4.0 g; yield = 97percent). 1H NMR (300 MHz, CDCl3) δ: 8.78 (s, IH), 8.11 (d, J = 8.4 Hz, 2H), 7.80 (d, J = 4.2 Hz, IH), 7.34 (d, J = 8.4 Hz, 2H), 7.73 (d, J = 4.2 Hz, IH), 2.42 (s, 3H). LC-MS: m/z = 308/310 (M+H)+.
95% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2 h; Example 1; 4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine; A slurry of 1 (307 mg, 2.00 mmol), Tosyl-chloride (418 mg, 2.20 mmol) and freshly ground K2CO3 (1.1 g, 8.0 mmol) in DMF (5.0 mL) was stirred at R.T. for 2 h. The mixture was partitioned between water and EtOAc and the organic phase was washed with brine (2.x.), dried (Na2SO4), filtered, and concentrated to provide the title compound (583 mg, 1.89 mmol, 95percent yield) as a white solid.
95% With sodium hydroxide In acetone at 20℃; Dissolve 4-chloro-pyrrolo[2,3-d]pyrimidine or intermediate 2 (10 mmol) in acetone (35 mL), add p-toluenesulfonyl chloride (1 mmol) in an ice bath, and then add 2.0 mol/L NaOH solution (12·5 mmol, 6.2 mL) was stirred overnight at room temperature. After the reaction was completed, a large amount of white solids precipitated, which was filtered. The filter cake was washed with 20 mL of acetone/water (1:1) and dried to obtain Intermediate 3. 4-Chloro-7-p-toluenesulfonyl 7H-pyrrolo[2,3-d]pyrimidine (3a) White solid, 95percent yield
90.1% With sodium hydroxide In water; acetone at -5 - 30℃; for 5 h; Example 7; Preparation of 4-chloro-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidine:; To a clean, dry, nitrogen-purged reactor were charged acetone (87.5 ml), p-toluenesulfonyl chloride (17.1 g, 0.09 mol) and 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (25.0 g, 0.16 mol). The reactor was cooled to between -5.0 to 5.00C and 2.5 M sodium hydroxide (78.1 ml) was added at a rate to maintain the temperature below 5.00C. The reactor was warmed to between 20-300C and stirred for a minimum of 5 hours. The resulting solids were isolated by filtration and washed with acetone/water (1 :1 , 25 ml each). After drying for a minimum of 12 hours under vacuum at 40-500C with slight nitrogen bleed, 44.9 g (90.1percent) of the title compound were isolated. Mp 140.2-147.70C. Anal. Calcd. for C13H10CIN3O2S: C, 50.73; H, 3.28; N, 13.65. Found: C,50.50; H, 3.06; N, 13.63. 1H NMR (400 MHz, CZ6-DMSO): δ 8.79 (s, 1 H), 8.09 (d, J=4.2 Hz, 1 H), 8.01 (d, J=8.5 Hz, 2H), 7.43 (d, J=8.5 Hz, 2H), 6.92 (d, J=4.2 Hz, 1 H), 2.32 (s, 3H). 13C NMR (400 MHz, dg- DMSO): δ 153.2, 152.7, 151.2, 147.2, 134.3, 131.0, 129.3, 128.5, 119.9, 103.9, 21.8.
90% With sodium hydroxide In water; acetone at 0 - 20℃; for 6 h; P-toluenesulfonyl chloride (67.5 g, 348 mmol, 1.10 eq.) and 4-chloro-7-Hpyrrolo[2,3-d]pyrimidine (50 g,320 mmol, 1.0 eq.) was dissolved in acetone (500 ml), sodium hydroxide solution (2 Min water, 200 ml, 1.20 eq.) was slowly added thereto at 0°C, and the reaction was stirred at 20°C for 6 hours to precipitate the solid. Filtration and washing with acetone and water gave the white target compound (90 g, yield = 90percent).
80% With sodium hydroxide In acetone at 20℃; A mixture of 4-c oro-7B~pyrfolo[2.s3-dJpyrimidme (10.0 g, 65 mraol), TsCl (13.7 g, 72 iirniol) and NaOH (40 ml,, 2N) in acetone (100 mL) was stirred at room temperature overnight. The resulting solid w s collected by filtration and washed with acetone and then with water to give the title compound as a white solid (16 g„ 80percent). H NM (400 MHz, CDCh) 5 8.7? (s, I B), 8.09 id J 8 0 Hz, 20), 7.77 (d, J 4.0 Hz, 1.H), 7.33 (4 J .0 1 . 2Π ). 6,70 (d, -4.0 1 / , 2H). 2.40 (s, 3H),
79.2% With triethylamine In dichloromethane at 20℃; for 5 h; The mixture of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (3.0g, 20mM), NEt3 (6.1g, 60mM) and p-toluene sulfonyl chloride (2.6g, 24mM) were stirred at room temperature in dichloromethane (100mL). After 5h, TLC analysis showed the complete consumption of 4-chloro-7H-pyrrolo [2, 3-d] pyrimidine. The reaction mixture was quenched by the addition of water (70mL). After quenching the reaction, the reaction mixture was poured into separator funnel and the aqueous layer was extracted with dichloromethane (100mL×3). The combined organic layers were evaporated in vacuo and purified by silica gel column chromatography to get the product 2a (4.9g, 79.2percent) as a white solid. ESI-MS m/z: 308.0 [M+H]+. 1H NMR (300MHz, DMSO‑d6): δ 2.37 (3H, s, CH3), 6.96 (1H, d, pyrrolyl-H, J=4.0Hz), 7.48 (2H, d, ArH, J=8.1Hz), 8.05 (2H, d, ArH, J=8.1Hz), 8.12 (1H, d, pyrrolyl-H, J=4.0Hz), 8.82 (1H, s, pyrimidiny-H).
45% With sodium hydroxide In water; acetone at 0 - 20℃; for 6 h; [0152] To a stirred solution of TsCI (1.35 g, 7.0 mmol) and 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1.0 g, 6.4 mmol) in acetone (10 mL) was added 2.0 M aqueous NaOH (8 mL, 16 mmol) at 0°C. The mixture was stirred at ambient temperature for 6 hours yielding a suspension. The solid product was collected by filtration and washed with acetone/water to afford the title compound as a white solid (0.9 g, 45percent). MS (ESl) calcd for C13H10C1N3025: 307.0; found:308.1[M+H]. 1H NMR (400 MHz, CDCI3) 6 8.77 (s, 1H), 8.09 (d, J = 8.0 Hz, 2H), 7.78 (d, J = 4.0Hz, 1H), 7.33 (d, J = 8.0 Hz, 2H), 6.71 (d, J = 4.0 Hz, 1H), 2.41 (s, 3H).
Ca. 2 kg With sodium hydroxide In acetone at -5 - 30℃; for 1 h; Autoclave; Large scale Autoclave, 3.5L of acetone, p-toluenesulfonyl chloride and 1.36kg 1kg compound 7, followed by stirring under cooling to 0 ~ -5 , maintained at below 5 2.5M sodium hydroxide solution was added dropwise 3.5L, warmed to completion of the dropwise 20-30 deg.] C for 1 h, TLC monitoring completion of the reaction was filtered, washed with 50percent acetone, slurried, filtered, drained, and dried in vacuo 50 ° to give compound 6 about 2kg.
124 g With tetrabutyl-ammonium chloride; potassium carbonate In dichloromethane; water at 20℃; A mixture of 66 g (0.43 mol) 4-chloro-7H-pyrrolo[2,3-d]pyrimidine, 607 g dichloromethane, 3.0 g tetrabutylammonium chloride, 90 g tosyl chloride, 85 g potassium carbonate and 381 g water is stirred efficiently at room temperature until reaction is complete. The phases are separated and the organic phase is washed with 340 g water. The organic phase is treated with 6.0 g of activated charcoal, completed with 318 g water and the organic solvent removed by distillation. The mixture is supplemented by 318 g heptane and the product is centrifuged, washed with heptane and water and vacuum dried at a temperature of not more than 8o°C, yielding 124 g (yield: 0.40 mol, 94percent conversion rate) of 4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine having a purity of 99.9 area-percent measured by HPLC.

Reference: [1] Patent: WO2010/123919, 2010, A2, . Location in patent: Page/Page column 49
[2] Patent: US2006/183761, 2006, A1, . Location in patent: Page/Page column 25
[3] Patent: CN107556318, 2018, A, . Location in patent: Paragraph 0101; 0108-0111
[4] Patent: WO2007/12953, 2007, A2, . Location in patent: Page/Page column 21
[5] Patent: CN103896946, 2018, B, . Location in patent: Paragraph 0080; 0081; 0082
[6] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 4, p. 1259 - 1263
[7] Patent: WO2016/44323, 2016, A1, . Location in patent: Paragraph 0258
[8] European Journal of Medicinal Chemistry, 2019, p. 243 - 255
[9] Patent: WO2016/126869, 2016, A1, . Location in patent: Paragraph 0152
[10] Patent: CN105294698, 2016, A, . Location in patent: Paragraph 0037
[11] Patent: WO2018/29641, 2018, A1, . Location in patent: Page/Page column 7-8
[12] Patent: WO2006/101783, 2006, A2, . Location in patent: Page/Page column 23-24
[13] Patent: WO2006/124462, 2006, A2, . Location in patent: Page/Page column 24; 31; 33-34
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Reference: [1] Patent: US2008/188483, 2008, A1, . Location in patent: Page/Page column 9
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Reference: [1] Patent: WO2018/29641, 2018, A1,
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  • [ 923036-30-0 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate In water at 100℃; for 16 h; Dissolve the compound (3R,4R)-1-benzyl-N,4-dimethyl-piperidin-3-amine (4.3 g, 19.7 mmol, 1.0 eq.)In 180 ml of water, the compound 4-chloro-7-(p-toluenesulfonyl)-pyrrolo[2,3-d]pyrimidine is then added thereto.(12.3 g, 39.2 mmol, 2.0 eq.) and potassium carbonate (16.6 g, 119 mmol, 6.0 eq.). The reaction is performed at 100oC for 16 hoursWhen it is, it is then cooled to room temperature. After adding three times with ethyl acetate (500ml), it is backwashed with water and brine.After drying over sodium sulfate and spin-drying, the resulting crude compound was isolated by column chromatography (ethyl acetate/petroleum ether = 1:1) to give pale yellowThe target compound (8.6 g, yield = 90percent).
Reference: [1] Patent: CN103896946, 2018, B, . Location in patent: Paragraph 0084; 0085; 0086
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 8012 - 8018
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YieldReaction ConditionsOperation in experiment
93% With N-ethyl-N,N-diisopropylamine In water; dimethyl sulfoxide at 107℃; for 9 h; Large scale Add SMA 11.0kg, SMB 12.8kg, DIPEA 19.5kg, DMSO to a 200L reactor50.0 kg, 15.0 kg of purified water, and the temperature was raised to 107°C. After the reaction is complete, add 24.0kg absolute ethanol to room temperature and addWater 30.0kg, stirring and decrystallization 2h, suction filtration, drying at 60±5°C, 17.2kg of white solid. Yield 93.0percent, SMB residue0.3percent, HPLC purity 98.9percent.
Reference: [1] Patent: CN107793418, 2018, A, . Location in patent: Paragraph 0042; 0043; 0044; 0045; 0046; 0047; 0049
  • 7
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YieldReaction ConditionsOperation in experiment
82.1% With potassium carbonate In water at 95 - 105℃; for 10 h; Example 8; Preparation of [(3R, 4R)-1-benzyl-4-methyl-piperidin-3-yl]-methyl-[7-(4-methyl-benzenesulfonyl)-7H- pyrrolo[2,3-d]pyrimidin-4-yl]amine:; To a clean, dry, nitrogen-purged reactor were charged 4-chloro-7-(4-methyl-benzenesulfonyl)- 7H-pyrrolo[2,3-d]pyrimidine (25.12 g, 0.082 mol), bis-(3R, 4R)-(1-benzyl-4-methyl-piperidine-3-yl)- methylamine di-p-toluoyl-L-tartaric acid (40.31 g, 0.041 mol), potassium carbonate (34.2 g, 0.245 mol), and water (125.6 ml). The mixture was heated to 95-1050C for a minimum of 10 hours, then cooled to 45-550C. Acetonitrile (25 ml) was charged and the slurry was held at 45-55°C for a minimum of 1 hour. The mixture was further cooled to 20-300C and stirred for a minimum of 5 hours. The resulting solids were isolated by filtration and washed with water (50 ml). After drying, 32.8 g (82.1percent) of the title compound were isolated.Mp 181.7-184.4C. Anal. Calcd. for C27H31N5O2S: C, 66.231; H, 6.38; N, 14.3. Found: C, 66.04; H, 6.47; N, 14.44. 1H NMR (400 MHz, CDCI3): δ 8.34 (s, 1 H), 8.06 (d, J=8.7 Hz, 2H), 7.43 (d, J=4.2 Hz, 1 H), 7.30-7.29 (m, 6H), 7.25-7.21 (m, 1H), 6.67-6.66 (m, 1H), 5.14 (bs, 1 H), 3.56-3.44 (m, 5H), 2.82-2.78 (m, 1H), 2.73 (bs, 1H), 2.58-2.55 (m, 1H), 2.38 (s, 3H), 2.31 (bs, 1 H), 2.12 (bs, 1H), 1.74 (bs, 1H), 1.69- 1.61 (m, 1 H), 0.90 (d, J=7.0 Hz, 3H). 13C NMR (400 MHz, CDCI3): δ 158.2, 152.9, 152.1 , 145.5, 138.7, EPO <DP n="23"/>135.4, 129.9, 129.1, 128.5, 128.4 127.3, 120.8, 106.6, 104.9, 63.7, 55.5 (b), 53.0 (b), 51.8 (b), 35.9 (b), 32.8, 31.4, 21.7 15.9 (b).
Reference: [1] Patent: WO2007/12953, 2007, A2, . Location in patent: Page/Page column 21-22
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YieldReaction ConditionsOperation in experiment
75 mg With potassium carbonate In water at 120℃; for 16 h; Inert atmosphere A mixture of chromium trioxide (49 mg, 0.49 mmol) in sulfuric acid (0.16 mL), acetic acid (0.16 mL) and water (0.11 mL) was added to a stirred solution of 14 (50 mg, 0.24 mmol) in acetone (0.5 mL) at 0 °C. After 2 h at <20 °C the reaction was basified to pH 12 with 33percent aq NH3 at 0 °C and extracted with ether (4*5 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in MeOH (0.17 mL) followed by addition of NH2Me (40percent in MeOH, 0.05 mL, 0.49 mmol) and Ti(OiPr)4 (0.08 mL, 0.27 mmol) at 0 °C. After stirring 30 min at room temperature, the reaction mixture was added sodium borohydride (46.5 g, 1.23 mol) in a small portion in 30 min at °0 C and stirred for an additional hour at the same temperature. The reaction mixture was filtered off to obtain crude amine. The crude amine in water (0.65 mL) was added K2CO3 (65 mg, 0.47 mmol) and 15 (120 mg, 0.39 mmol), and the mixture was refluxed (120 °C) for 16 h under argon. After cooling to rt, the resulting mixture was added CH2Cl2 (5 ml) and sonicated crush the solid. The mixture was extracted with CH2Cl2 (4*5 mL) and the combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexanes, 1:1) to give trans-16 (8 mg, 7percent) as a white solid and cis-16 (75 mg, 63percent) as a white solid. Rf = 0.4 (trans-16), 0.48 (cis-16) (EtOAc/hexanes, 1:1). trans-16: 1H NMR (400 MHz, CDCl3) δ: 8.35 (s, 1H), 8.03 (d, J = 8.8 Hz, 2H), 7.37 (d,J = 4 Hz, 1H), 7.32–7.18 (m, 7H), 6.53 (br s, 1H), 3.56, 3.45 (ABq, JAB = 12.8 Hz, 2H), 3.08 (s, 3H), 2.90–2.84 (m, 2H), 2.36 (s, 3H), 2.10–1.95 (m, 2H), 1.80–1.65 (m, 3H), 1.50–1.39 (m, 1H), 0.81 (d, J = 6 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ: 158.0, 152.8, 151.7, 145.2, 138.1, 135.1, 129.6, 129.0, 128.2, 127.1, 120.9, 105.6, 104.7, 62.8, 55.4, 53.4, 33.6, 33.4, 21.6, 18.3. cis-16: [a]D28 = +19.3(c 1.0 CHCl3). 1H NMR (400 MHz, CDCl3) δ: 8.31 (s, 1H), 8.03 (d,J = 8 Hz, 2H), 7.40 (d, J = 3 Hz, 1H), 7.27–7.17 (m, 7H), 6.63 (d,J = 3.2 Hz, 1H), 5.16 (br s, 1H), 3.56 (s, 3H), 3.47, 3.42 (ABq, JAB = 13.2 Hz, 2H), 2.79–2.76 (m, 1H), 2.75 (br s, 1H), 2.52 (d, J = 10.8, 1H), 2.36 (s, 2H), 2.35–2.22 (m, 1H), 2.10–2.03 (m, 1H), 1.70–1.610 (m, 2H), 0.87 (d, J = 7.2 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ: 189.3, 157.9, 152.5, 151.8, 145.2, 135.1, 129.6, 128.9, 128.2, 128.1, 127.1, 120.6, 106.2, 104.6, 63.5, 55.2 (br), 53.1 (br), 51.6 (br), 35.8 (br), 32.5, 31.2, 21.6, 15.7 (br). HRMS (ESI) calcd for C27H31N5O2S [M+H]+: 490.2277, found: 490.2273.
Reference: [1] Tetrahedron Asymmetry, 2017, vol. 28, # 1, p. 105 - 109
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2-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

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