Structure of 148760-75-2
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CAS No. : | 148760-75-2 |
Formula : | C12H14N2O2 |
M.W : | 218.25 |
SMILES Code : | O=C(N1C=CC2=C1C=CN=C2)OC(C)(C)C |
MDL No. : | MFCD11976180 |
InChI Key : | PKYJYPDHSCLTJO-UHFFFAOYSA-N |
Pubchem ID : | 20042876 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 61.93 |
TPSA ? Topological Polar Surface Area: Calculated from |
44.12 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.49 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.2 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.82 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.51 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.51 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.11 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.8 |
Solubility | 0.348 mg/ml ; 0.00159 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.76 |
Solubility | 0.379 mg/ml ; 0.00174 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.99 |
Solubility | 0.222 mg/ml ; 0.00102 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.07 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.94 |
* 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 |
---|---|---|
100% | With dmap; In acetonitrile; at 20℃; for 18h; | Step A: Preparation of tert-butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate: To a stirred mixture of 1H-pyrrolo[3,2-c]pyridine (2.3 g, 20 mmol) and N,N-dimethylpyridin-4-amine (2.4 g, 20 mmol) in CH3CN (20 mL) was added Boc-anhydride (3.9 g, 18 mmol). The mixture was stirred for 18 hours at ambient temperature. The reaction was concentrated in vacuo, and then purified by Biotage Flash 40S, eluding with 1:1 EtOAc/hexanes. The product was obtained as a colorless oil (4.0 g, 101%). |
98.2% | With triethylamine; In dichloromethane; at 25℃; for 12h;Inert atmosphere; | To the solution of lH-pyrrolo[3,2-c]pyridine (LXXIV) (24 g, 203 mmol) and TEA (62 g, 609 mmol) in DCM (200 mL) was added (Boc)20 (48.8 g, 223.5 mmol) in portions at 25C under N2. The mixture was stirred at 25C for 12 h. The reaction mixture was then diluted with DCM and dried to give the crude product. The residue was purified by column chromatography (S1O2, PE/EtOAc = 2/1, Rf= 0.40) to give fert-butyl lH-pyrrolo[3,2-c]pyridine-l- carboxylate (C) (43.5 g, 199.3 mmol, 98.2% yield) as a light yellow oil. ESIMS found for C12H14N2O2 mlz 219.1 (M+H). |
98.2% | With triethylamine; In dichloromethane; at 25℃; for 12h;Inert atmosphere; | To the solution of lH-pyrrolo[3,2-c]pyridine (LXXIV) (24 g, 203 mmol) and TEA (62 g, 609 mmol) in DCM (200 mL) was added (Boc)20 (48.8 g, 223.5 mmol) in portions at 25C under N2. The mixture was stirred at 25C for 12 h. The reaction mixture was then diluted with DCM and dried to give the crude product. The residue was purified by column chromatography (S1O2, PE/EtOAc = 2/1, Rf = 0.40) to give tert-buty lH-pyrrolo[3,2-c]pyridine- 1-carboxylate (C) (43.5 g, 199.3 mmol, 98.2% yield) as a light yellow oil. ESIMS found for C12H14N2O2 mlz 219.1 (M+H). |
98.2% | With triethylamine; In dichloromethane; at 25℃; for 12h;Inert atmosphere; | To the solution of lH-pyrrolo[3,2-c]pyridine (XCI) (24 g, 203 mmol) and TEA (62 g, 609 mmol) in DCM (200 mL) was added (Boc)20 (48.8 g, 223.5 mmol) in portions at 25C under N2. The mixture was stirred at 25C for 12 h. The reaction mixture was then diluted with DCM and dried to give the crude product. The residue was purified by column chromatography (S1O2, PE/EtOAc = 2/1, Rf = 0.40) to give fert-butyl lH-pyrrolo[3,2-c]pyridine- 1-carboxylate (CXVII) (43.5 g, 199.3 mmol, 98.2% yield) as a light yellow oil. ESIMS found for C12H14N2O2 mlz 219.1 (M+H). |
98.2% | With triethylamine; In dichloromethane; at 25℃; for 12h; | Step 1 [0703] To the solution of lH-pyrrolo[3,2-c]pyridine (LXXIV) (24 g, 203 mmol) and TEA (62 g, 609 mmol) in DCM (200 mL) was added (Boc)20 (48.8 g, 223.5 mmol) in portions at 25C under N2. The mixture was stirred at 25C for 12 h. The reaction mixture was then diluted with DCM and dried to give the crude product. The residue was purified by column chromatography (S1O2, PE/EtOAc = 2/1, Rf = 0.40) to give fert-butyl lH-pyrrolo[3,2-c]pyridine- 1-carboxylate (C) (43.5 g, 199.3 mmol, 98.2% yield) as a light yellow oil. ESIMS found for C12H14N2O2 mlz 219.1 (M+H). |
97% | With triethylamine; at 0℃; for 6h; | To a solution of <strong>[271-34-1]5-azaindole</strong> (5.00 g) and Et3N (12 mL) was added (Boc)20 ( 14 mL) dropwise at 0C. The mixture was stirred for 6 h, then diluted with water and extracted with EtOAc. The organic layer was dried over Na2S04 for 1 h and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 3: 1 (v/v) PE/EA) to give the title compound as transparent liquid (9.00 g, 97.00 %). The compound was characterized by the following spectroscopic data: ? NMR (400 MHz, CDC13) ?: 1.65 (s, 9H), 6.62 (d, J = 3.6 Hz, 1H), 7.25 (d, J = 5.3 Hz, 1 H), 7.50 (d, J = 3.5 Hz, 1H), 8.42 (d, J= 5.3 Hz, 1 H), 9.43 (s, lH) ppm. |
97% | With triethylamine; at 0℃; for 6h; | To a solution of <strong>[271-34-1]5-azaindole</strong> (5.00 g) and Et3N (12 mL) was added (Boc)2O (14 mL) dropwise at 0 C. The mixture was stirred for 6 h, then diluted with water and extracted with EtOAc. The organic layer was dried over Na2SO4 for 1 h and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 3:1 (v/v) PE/EA) to give the title compound as transparent liquid (9.00 g, 97.00%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ: 1.65 (s, 9H), 6.62 (d, J=3.6 Hz, 1H), 7.25 (d, J=5.3 Hz, 1H), 7.50 (d, J=3.5 Hz, 1H), 8.42 (d, J=5.3 Hz, 1H), 9.43 (s, 1H) ppm. |
92.4% | With dmap; In acetonitrile; at 20℃; for 2.5h; | Dimethylaminopyridine (DMAP) (2.08 g, 16.9 mmol) in acetonitrile (20 mL) was added drop wise to <strong>[271-34-1]5-azaindole</strong> (2.0 g, 16.9 mmol) in acetonitrile (70 mL) at room temperature. After stirring for 2 hours, di-ieri-butyldicarbonate (3.68 g, 16.9 mmol) was added in portion at same temperature. After 2.5 hours, the solvent was evaporated under reduced pressure and the residue (5.4 g) was purified by column chromatography (silica gel, ethyl acetate/heptane 1/10 to 1/2) to provide pyrrolo[3,2-c]pyridine-l- carboxylic acid tert-butyl ester (2.72 g, 92.4% yield) as a bright yellow oil. 1H NMR (Field: 300 MHz, Solvent: CD3OD/TMS) δ (ppm): 8.87 (s, 1H), 8.48 (d, 1H, J= 5.7 Hz), 7.98 (d, 1H, J = 5.1 Hz), 7.60 (d, 1H, J = 3.3 Hz), 6.63 (d, lH, J = 3.0 Hz), 1.68 (s, 9H). 13C NMR (Field: 75 MHz, Solvent: CDCI3/TMS) δ (ppm): 148.82, 143.75, 143.51 , 139.50, 126.69, 109.83, 105.46, 84.60, 28.05. |
EXAMPLE 10 Preparation of 1-tert-butoxycarbonyl-1H-pyrrolo[3,2-c]pyridine Following the same method as that described in Example 1 but starting from 22.6 g (0.2 mol) of 1H-pyrrolo[3,2-c]pyridine and 55 ml (0.24 mol) of tert-butyl dicarbonate, there were obtained 42.5 g of a brown oil which crystallized in the refrigerator. By chromatographic purification of an analytical sample, 1-tert-butoxycarbonyl-1H-pyrrolo[3,2-c]pyridine was obtained in the form of a cream-coloured powder. M.P.: 65 C. | ||
With dmap; In dichloromethane; for 1.25h; | To lH-pyrrolo[3,2-c]pyridine (500 mg, 4.2 mmol) in dry DCM (2 mL) were added DMAP (569 mg, 4.7 mmol, in 2 mL dry DCM ) and di-tert-butyl carbonate ( 1.02 g, 4.7 mmol, in 2 mL dry DCM). The mixture was stirred over night and extracted with IM aq HCl (20 mL) and DCM (3x 20 mL). The organic lay- ers were combined, dried (Na2Sθ4), filtered and concentrated to give 333 mg of a white solid, tert-butyl lH-pyrrolo[3,2-c]pyridine- l-carboxylate. MS (ESI+) for C12H 14N2O2 m/z 219 (M+H)+. Part of the material (163 mg, 0.75 mmol) was suspended in dry THF (5 mL) and triisopropyl borate (0.21 mL, 0.90 mmol) was added and the mixture was cooled on ice. 1.8 M LDA (0.50 mL, 0.90 mmol) was added dropwise over 20 minutes. Additional LDA (0.85 mL, 1.52 mmol, 2 additions) was added over 45 minutes to complete the reaction. An aliquot of 0.9 mL was added to a mixture of 6-chloro-N-(4-[(3R)-3- (dimethylamino)pyrrolidin- l-yl]carbonyl}-2-methoxyphenyl)pyrazin-2-amine (20 mg, 0.05 mmol), K2CO3 (1 1 mg, 0.13 mmol) and Pd(PPh3J4 (6 mg, 0.05 mmol) in MeCN/water (7:3, 4 mL). The mixture was irradiated in a microwave oven at 120 0C for 10 minutes. This was performed twice, using a total of 40 mg of 6-chloro-N-(4-[(3R)-3-(dimethylamino)pyrrolidin- l-yl]carbonyl}-2- methoxyphenyl)pyrazin-2-amine. The reactions were combined, the solvent was evaporated and the residue was extracted with DCM (2x 10 mL) and satu- rated aq Na2CO3 ( 10 mL). The organic layers were combined, dried (Na2Sθ4), filtered and concentrated. The material was purified twice by preparative HPLC <n="167"/>(XTerra C18, 50 mM NH4HCO3 pH 10, MeCN). The title compound was obtained as a light yellow solid (7 mg) . HPLC 99%(System A), 100%(System B).IH NMR (400 MHz, MeOD). Dppm 1.75 - 1.95 (m, 1 H) 2.12 - 2.24 (m, 1 H) 2.25 (s, 3 H) 2.34 (s, 3 H) 2.75 - 2.96 (m, 1 H) 3.41 - 3.54 (m, 1 H) 3.57 - 3.91 (m, 3 H) 3.98 (s, 3 H) 7.22 (d, J= 1.76 Hz, 1 H) 7.25 - 7.31 (m, 1 H) 7.33 (s, 1 H) 7.48 - 7.52 (m, 1 H) 8.17 (d, J=5.77 Hz, 1 H) 8.27 (s, 1 H) 8.51 (s, 1 H) 8.58 - 8.68 (m, 1 H) 8.84 (d, J=LOO Hz, 1 H). MS (ESI+) calcd for C2SH27N7O2 457.2226, found 457.2222. | |
With dmap; In dichloromethane; at 20℃; for 12h;Inert atmosphere; | Step C: 5-Azaindole (10.00g, 84.65mmol, 1.00eq), Boc2O (19.40g, 88.88mmol, 20.42mL, 1.05eq) and 200mLdichloromethane were added to a single-neck round bottom flask, followed by addition of DMAP (1.03g, 8.47mmol,0.10eq) under nitrogen atmosphere. The reaction solution was stirred at 20C for 12 hours, then concentrated andpurified by silica gel column chromatography (EA/PE=0%-40%) to give 95. 1H NMR (400MHz, CHLOROFORM-d) δ8.89 (s, 1H), 8.47 (d, J=6.0 Hz, 1H), 7.98 (d, J=5.6 Hz, 1H), 7.61 (d, J=3.6 Hz, 1H), 6.65 (d, J=3.6 Hz, 1H), 1.69 (s, 9H). | |
1.76 g | With triethylamine; In acetonitrile; at 0 - 20℃;Inert atmosphere; | To a solution of triethylamine (0.65 ml, 4.66 mmol) and <strong>[271-34-1]5-azaindole</strong> (1.00 g, 8.46 mmol) in MeCN (20 ml) stirring at 0 00 was added di-teit-butyl dicarbonate (0.97 ml,4.23 mmol) dropwise under nitrogen with stirring. The reaction was allowed to warm to room temperature and left to stir over the weekend. Further di-teit-butyl dicarbonate (0.97 ml, 4.23 mmol) was added and stirring continued for 6 hours. The reaction mixture was concentrated under reduced pressure and the oil obtained taken up in DCM and washed with water. The mixture was passed through a hydrophobic frit and solvent removed under reduced pressure to afford teit-butyl pyrrolo[3,2-c]pyridine-1-carboxylate (P62) (1.76 g), LCMS ES 219 [M+H], Rt = 1.19 mins (Generic Basic Method). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With trifluoroacetic acid; In dichloromethane; at 20℃; for 1.5h; | To a solution of 4-aminopyridine (1a, 37.65 g, 0.4 mole) in HOAc (200 mL) was added iodine monchloride (130 g, 0.8 mole) portionwise. The reaction mixture was stirred at 45 C. for 20 h, then diluted with water (500 mL). The mixture was cooled to 0 C., and basified 30% NaOH to pH=9-10. The solution was extracted with EtOAc (1 L×2) and the combined extracts were washed with 15% Na2S2O3 (400 mL×2), water, brine, dried over Na2SO4, and evaporated in vacuo to give 1b (62 g) as a light yellow solid. ES-MS m/z 221 (MH+). [0185] Into a pressure flask was added 1b (4.4 g, 20 mmol), cupric iodide (228 mg, 1.2 mmol), (trimethylsilyl)acetylene (7.08 g, 72 mmol), triethylamine (200 mL) and DMF (80 mL). The mixture was stirred under nitrogen for 10 min, followed by addition of Pd(PPh3)2Cl2 (0.84 g, 1.2 mmol). The mixture was then stirred to 70 C. for 5 h, and then diluted with ethyl acetate (600 mL). The solution was washed with H2O (250 mL×2), brine (250 mL), dried over Na2SO4, and evaporated in vacuo to give crude product which was purified by flash chromatography (100% CH2Cl2 to 2% MeOH in CH2Cl2) to afford Compound 1c (2. 97 g, 78%) as a light brown solid. 1H NMR (CDCl3) δ 8.37 (s, 1H), 8.13 (d, J=5.7 Hz, 1H), 6.53 (d, J=5.6 Hz, 1H), 4.67 (bs, 2H), 0.27 (s, 9H). ES-MS m/z 191 (MH+). [0186] Into an ice-cold solution of 1c (1.35 g, 7.1 mmol) in THF (50 mL) was added 95% NaH (1.86 g, 8.5 mmol). The mixture was stirred at 0 C. for 10 min, rt for 10 min, then cooled back to 0 C. (Boc)2O (1.86 g, 8.5 mmol) was added and the mixture was stirred at 0 C. for 30 min and then rt for 2 h. Additional 95% NaH (0.08 g, 3.5 mmol) and (Boc)2O (0.2 g, 0.92 mmol) were added and the mixture was stirred at rt for another 2 h. The reaction was then quenched slowly with saturated NaHCO3 (10 mL), extracted with ethyl acetate (200 mL×2). The organic layer was washed with brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (EtOAc/hexane; 1:3) to give 1d (0.67 g). ES-MS m/z 219 (MH+). [0187] To a solution of 1d (1.3 g, 4.5 mmol) in DMF (20 mL) was added cupric iodide (0.85 g, 4.5 mmol). The mixture was stirred at 80 C. for 6 h and then filtered. The filtrate was extracted with ethyl acetate (100 mL×3), and the organic layer was washed with H2O, brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (Ethyl acetate/hexane; 1:3) to give Compound 1e (0.25 g, 26%). 1H NMR (CDCl3) δ 8.89 (s, 1H), 8.47 (d, J=5.8 Hz, 1H), 7.98 (d, J=5.7 Hz, 1H), 7.62 (d, J=3.7 Hz, 1H), 6.66 (d, J=3.7 Hz, 1H), 1.69 (s, 9H). ES-MS m/z 219 (MH+). [0188] To a solution of 1e (0.178 g, 0.82 mmol) in methylene chloride (5 mL) was added TFA (1.0 mL) slowly. The mixture was stirred at rt for 1.5 h, and The solvent was evaporated to obtain 5-azaindole 1f as a white solid (0.18 g, 95%). 1H NMR (CDCl3) δ 8.97 (s, 1H), 8.31 (d, J=5.7 Hz, 1H), 7.35 (d, J=5.7 Hz, 1H), 7.29 (m, 1H), 6.68 (d, J=3.3 Hz, 1H). ES-MS m/z 119 (MH+). [0189] A mixture of Compound 1f (0.26 g, 2.2 mmol) and cesium carbonate (1.43 g, 4.4 mmol) in DMF (10 mL) was stirred at rt for 10 min, and then 3-methoxypropylbromide (0.40 g, 2.64 mmol) was added. The reaction mixture was stirred at 60 C. for 3 h. The solvent was evaporated and the residue was partitioned between EtOAc (150 mL) and water (100 mL). The organic layer was washed with water (3×50 mL), brine (2×50 mL), then dried (Na2SO4) and evaporated in vacuo to give a brown oil. The crude product was purified by flash column chromatography (from 100% DCM to DCM/MeOH/NH4OH; 97:3:0.3) to afford Compound 1g (0.26 g, 62%) as light brown oil. 1H NMR (CDCl3) δ 8.91 (s, 1H), 8.31 (d, J=5.8 Hz, 1H), 7.27 (s, 1H), 7.11 (d, J=3.2 Hz, 1H), 6.60 (d, J=3.3 Hz, 1H), 4.25 (t, J=6.7 Hz, 2H), 3.32 (s, 3H), 3.25 (t, J=5.7 Hz, 2H), 2.05 (m, 2H). ES-MS m/z 191(MH+). [0190] Oxalyl chloride (3 mL) was added slowly to a solution of compound 1g (0.22 g, 1.14 mmol) in ether (5 mL). The mixture was heated to 48 C. in a pressure tube overnight. TLC shown that some starting materials were still present. Additional 0.5 mL of oxalyl chloride was added and stirring was continuted at 48 C. for another night. The mixture was then cooled down to rt, to which methanol (3 mL) was added. The mixture was heated to 48 C. and stirred for 2 h. The volatiles removed under vacuo and the residue was purified by flash chromatography (from 100% DCM to DCM/MeOH/NH4OH; 97:3:0.3) to afford Compound 1h (0.15 g, 48%) as a white solid. 1H NMR (CDCl3) δ 8.51 (d, J=5.8 Hz, 1H), 8.44 (s, 1H), 7.37 (m, 1H), 4.34 (t, J=6.8 Hz, 2H), 3.97 (s, 3H), 3.35 (s, 3H), 3.30 (t, J=5.7 Hz, 2H), 2.12 (m, 2H). ES-MS m/z 277 (MH+). [0191] The α-ketoester Compound 1h (53.8 mg, 0.20 mmol) and amide Compound 1i (23 mg, 0.14 mmol) were combined in dry THF (3 mL) under argon and cooled with an ice bath as a solution of 1.0 M potassium t-butoxide in THF (1 mL, 1 mmol) was added dropwise. The mixture was stirred at 0 C. for 30 min, then rt for 2 h. Th... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With 10 wt% Pd(OH)2 on carbon; hydrogen; acetic acid; In 2-methoxy-ethanol; at 70.0℃; under 15001.5 Torr; for 24.0h; | To a solution of tert-butyl l H-pyrrolo[3,2-c]pyridine-l-carboxylate (2.55 g) in the mixture solvent of glycol monomethyl ether (40 mL) and AcOH (1 mL) was added a catalytic amount of Pd(OH)2/C. The suspension was heated at 70 C for 24 h under H2 (2.0 MPa) and filtered. The filtrate was concentrated in vacuo andthe residue was chromatographed with a silica gel column (eluting agent: 10: 1 (v/v) CH2Cl2/MeOH) to give the product as viscous liquid (2.64 g, 100.00 %). |
100% | With 10 wt% Pd(OH)2 on carbon; hydrogen; In acetic acid; at 70.0℃; under 15001.5 Torr; for 24.0h; | To a solution of tert-butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate (2.55 g) in the mixture solvent of glycol monomethyl ether (40 mL) and AcOH (1 mL) was added a catalytic amount of Pd(OH)2/C. The suspension was heated at 70 C. for 24 h under H2 (2.0 MPa) and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/MeOH) to give the product as viscous liquid (2.64 g, 100.00%). |
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