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[ CAS No. 1193-62-0 ]

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Chemical Structure| 1193-62-0
Chemical Structure| 1193-62-0
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CAS No. :1193-62-0MDL No. :MFCD00817048
Formula : C6H7NO2 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :125.13Pubchem ID :136930
Synonyms :

Computed Properties of [ 1193-62-0 ]

TPSA : 42.1 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.17 Rotatable Bond Count : 2

Safety of [ 1193-62-0 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1193-62-0 ]

  • Upstream synthesis route of [ 1193-62-0 ]
  • Downstream synthetic route of [ 1193-62-0 ]

[ 1193-62-0 ] Synthesis Path-Upstream   1~47

  • 1
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  • [ 1193-62-0 ]
YieldReaction ConditionsOperation in experiment
85% at 0 - 35℃; for 24.5 h; To a solution of pyrrole-2-carboxylic acid (1) (16.65 g, 0.15 mol)in 10 mL of MeOH was added 50 mL of SOCl2 dropwise within30 min at 0 C. Subsequently, the reaction mixture was stirred at35 C for 24 h. Then, the solvent was evaporated in vacuo, andthe residue was purified by column chromatography using ethylacetate/petroleum ether as eluent, giving intermediate 2 as a whitesolid, yield 85percent, mp: 72–73 C.
79% With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 20 - 60℃; for 72 h; Example 36-1
Preparation for methyl 1H-pyrrole-2-carboxlate
A suspension of 1H-pyrrole-2-carboxylic acid (5.5g, 49.5mmol), WSCI*HCl (12.2g, 63.6mmol), HOBt (8.4g, 62.2mmol), methanol (7.0g, 218mmol) and 4-dimethylaminopyridine (3.0g, 24.5mmol) in dimethylformamide (60ml) was stirred for 70 hours at room temperature and for 2 hours at 60°C.
To the reaction mixture was added an aqueous 5percent potassium hydrogensulfate solution and the mixture was extracted with ethyl acetate/toluene (1/1)..
The organic layer was washed with an aqueous saturated sodium hydrogencarbonate solution, and an aqueous saturated sodium chloride solution, and dried over magnesium sulfate..
The solvent was removed and the residue was purified with silica gel chromatography (hexane:ethyl acetate=5:13:1) to give the subject compound (4.88g, 79percent).1H NMR (CDCl3, 400 MHz) δ 9. 08 (brs, 1 H), 6. 90 - 6. 98 (m, 2 H), 6.25 - 6.29 (m, 1 H), 3.86 (s, 3 H).
65% With chloro-trimethyl-silane In methanol at 20℃; Method I Synthesis of 5-tert-Butyl-3-(3-p-tolyl-ureido)-1H-pyrrole-2-carboxylic acid methyl ester. (Example 24) [Show Image] Step 1; Chlorotrimethylsilane (17.9 mL, 141 mmol, 2.5 equiv) is added in one portion to a solution of pyrrole-2-carboxylic acid (6.28 g, 56.5 mmol) in dry methanol (100 mL) under N2 at rt. After stirring overnight, the reaction mixture is concentrated in vacuo, redissolved in dichloromethane, washed with water, dried (Na2SO4) and concentrated to give 4.62 g of methyl pyrrole-2-carboxylate as a tannish semi-crystalline solid (65percent), which was used without further purification. 1H NMR (CDCl3) d 9.3 (br s, 1H), 6.96 (br m, 1H), 6.92 (br m, 1H), 6.29 (br q, 1H), 3.86 (s, 3H).
65% at 20℃; To a solution of pyrrole-2-carboxylic acid (6.28 g, 56.5 mmol) in anh. MeOH (100 mL) under N2 at room temp. was added TMSCl (17.9 mL, 141 mmol, 2.5 equiv) in one portion. After stirring overnight, the reaction mixture was concentrated under reduced pressure, redissolved in CH2Cl2, washed with water, dried (Na2SO4) and concentrated to give methyl pyrrole-2-carboxylate as a tannish semi-crystalline solid (4.62 g, 65percent): 1H NMR (CDCl3) δ 3.86 (s, 3H), 6.29 (br q, 1H), 6.92 (br m, 1H), 6.96 (br m, 1H), 9.30 (br s, 1H). This material was used in the next step without further purification.

Reference: [1] Canadian Journal of Chemistry, 2002, vol. 80, # 12, p. 1662 - 1667
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 22, p. 7091 - 7100
[3] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 20, p. 2997 - 3003
[4] Patent: EP1386913, 2004, A1, . Location in patent: Page 88
[5] Patent: EP986382, 2008, B1, . Location in patent: Page/Page column 23
[6] Patent: EP1019040, 2004, B1, . Location in patent: Page/Page column 31
[7] Journal of Natural Products, 2012, vol. 75, # 10, p. 1765 - 1776
[8] Patent: WO2006/23844, 2006, A2, . Location in patent: Page/Page column 92
  • 2
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  • [ 35302-72-8 ]
  • [ 1193-62-0 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #2: at 20℃; for 2.5 h;
In dry methanol (40 mL), sodium (0.14 g, 6.20mmol) was dissolved and trichloroacetyl-1H-pyrrole (8) (9.440 g, 44.43 mmol) was added insmall quantities over 30 min. Then the reaction mixture was stirred for additional 2 hours atroom temperature, and then the solvent was removed and resulting crystals were dissolved indiethyl ether (50 mL). Ether solution was washed with HCl (4 mL, 3 N) and then NaHCO3(10 mL) solution. Then the organic phase was dried over Na2SO4. After the filtration andevaporation of the solvent, the crude product was purified via column chromatography (SiO2,ethyl acetate/hexane, 2:3) and concentrated in vacuum to obtain methyl 1H-pyrrole-2-carboxylate 9 (4.83 g, 87percent) which was crystallized from ethyl acetate/hexane as colorlesspellets
Reference: [1] Green Chemistry, 2011, vol. 13, # 1, p. 102 - 108
[2] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 825 - 834
[3] Chemical Communications, 1999, # 9, p. 843 - 844
[4] Chemistry - A European Journal, 2000, vol. 6, # 4, p. 709 - 718
[5] Tetrahedron Letters, 2005, vol. 46, # 12, p. 2041 - 2044
  • 3
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  • [ 1193-62-0 ]
YieldReaction ConditionsOperation in experiment
92% at 23℃; for 0.666667 h; Inert atmosphere To a freshly prepared solution of NaOCH3 from sodium (0.25 g, 10.9 mmol) and anhydrous CH3OH (20 mL) was added in batches 2,2,2-trichloro-1-(1H-pyrrol-2-yl)-ethanone9 (4.70 g, 22.0 mmol) over a period of 10 min in an atmosphere of N2. After stirring for 30 min at 23 °C the solvent was removed under reduced pressure (11 mbar, 40 °C). The dark residue was partitioned between Et2O (50 mL) and 2 m aq. HCl (15 mL). The organic layer was separated and kept. The aqueous layer was extracted with Et2O (2 .x. 10 mL). Combined organic layer and extracts were washed with satd. aq. NaHCO3 (15 mL) and dried (MgSO4). The solvent was removed under reduced pressure (10 mbar, 40 °C) to afford a purple solid which was purified by column chromatography (Et2O). Yield: 2.56 g (20.0 mmol, 92 percent), colourless solid, mp 74-77 °C. IR (KBr) (cm-1) 3290, 3122, 2953, 1685, 1559, 1446, 1406, 1128. 1H NMR (CDCl3, 600 MHz) d 3.86 (s, 3 H), 6.26-6.28 (m, 1 H), 6.91-6.93 (m, 1 H), 6.95-6.96 (m, 1 H), 9.22 (br.s, 1 H, NH). 13C NMR (CDCl3, 150 MHz) d 51.6, 110.6, 115.4, 122.8, 123.0, 161.7. MS (EI) m/z 125 (66), 94 (100), 66 (36).
88% at 0℃; for 3 h; To a stirred solution of 11 (31.87 g, 0.150 mol) in methanol (50 mL) was added a solution of NaOMe solution in methanol (50 mL), prepared by dissolving of Na (3.46 g, 0.150 mol) in methanol, dropwise at 0 °C for 3 h. The solvent was evaporated and diluted HCl (50 mL) was added to residue. The mixture was extracted with ethyl acetate (3 × 150 mL) and dried over MgSO4. Evaporation of solvent gave the ester 12 as a brown solid (16.5 g, 88percent).
Reference: [1] Tetrahedron, 2011, vol. 67, # 22, p. 4048 - 4054
[2] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 897 - 905
[3] European Journal of Organic Chemistry, 1999, # 9, p. 2397 - 2403
[4] Journal of Organic Chemistry, 2005, vol. 70, # 20, p. 8231 - 8234
[5] Synthesis, 2004, # 14, p. 2367 - 2375
[6] Chinese Chemical Letters, 2013, vol. 24, # 7, p. 619 - 621
[7] Tetrahedron Letters, 2016, vol. 57, # 32, p. 3629 - 3634
  • 4
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YieldReaction ConditionsOperation in experiment
89% With β-cyclodextrin; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water at 20℃; for 4 h; General procedure: To an aqueous solution of βcyclodextrin (1.0 mmol of β-CD in 5mL of water), IBX (2.0 mmol), N-benzylpyrrolidine (1.0 mmol) was added while stirring, and stirring was continued for the stipulated reaction time as shown in the table at room temperature. After completion of reaction as indicated by TLC, the reaction mixture was extracted with ethylacetate (3 X 5mL), the combined organic layers were washed with saturated brine solution, dried and concentrated in vacuum. The crude product was purified by column chromatography on silica gel using hexane/ethyl acetate (9:1) as an eluent.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 34, p. 4481 - 4484
  • 5
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YieldReaction ConditionsOperation in experiment
74% With sodium In methanol for 12 h; Heating / reflux Sodium metal (6.9 g, 0.30 mol) was dissolved in anhydrous methanol (1.5 L) and then 2-(trichloroacetyl)pyrrole (223 g, 1.5 mol) dissolved in anhydrous methanol (500 mL) was added. The mixture was heated at reflux for 12 hour. The methanol was removed under reduced pressure and the product crystallized by pouring the residue into a 3:1 ice-water/methanol mixture (2 L). The light brown solid was collected by vacuum filtration and dried to afford 97.2 g (0.78 mol, 74percent) of the title compound. 1H-NMR (CDCl3): ? 7.00 (m, 1H), 6.79 (d, 1H), 6.15 (dd, 1H), 3.74 (s, 1H).
Reference: [1] European Journal of Organic Chemistry, 2008, # 2, p. 324 - 329
[2] Patent: US6696575, 2004, B2, . Location in patent: Page column 3;4;17;18;11
[3] Patent: US2012/114696, 2012, A1,
  • 6
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Reference: [1] Chemische Berichte, 1911, vol. 44, p. 3168
[2] Patent: US6344476, 2002, B1,
[3] Patent: US4282242, 1981, A,
[4] Patent: US6187799, 2001, B1,
[5] Patent: US6335445, 2002, B1, . Location in patent: Page column 106
  • 7
  • [ 294659-30-6 ]
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Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 9, p. 1071 - 1074
  • 8
  • [ 57850-02-9 ]
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Reference: [1] Patent: US2013/324501, 2013, A1, . Location in patent: Paragraph 0247; 0249
[2] Patent: WO2013/182451, 2013, A1, . Location in patent: Page/Page column 41
  • 9
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Reference: [1] Patent: US2012/114696, 2012, A1,
[2] Patent: US2012/114696, 2012, A1,
  • 10
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Reference: [1] Patent: US4737513, 1988, A,
  • 11
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Reference: [1] Tetrahedron, 1986, vol. 42, # 13, p. 3723 - 3730
  • 12
  • [ 109-97-7 ]
  • [ 124-41-4 ]
  • [ 76-02-8 ]
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Reference: [1] Organic Process Research and Development, 2010, vol. 14, # 4, p. 787 - 798
  • 13
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Reference: [1] Tetrahedron, 2011, vol. 67, # 46, p. 8851 - 8859
  • 14
  • [ 186581-53-3 ]
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Reference: [1] Tetrahedron, 1992, vol. 48, # 8, p. 1457 - 1464
[2] Justus Liebigs Annalen der Chemie, 1955, vol. 593, p. 91,109
[3] Journal of the Chemical Society, 1958, p. 4458,4462
[4] Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1475 - 1480
[5] Chemistry Letters, 1991, # 9, p. 1541 - 1542
[6] Tetrahedron Letters, 2002, vol. 43, # 14, p. 2589 - 2592
  • 15
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Reference: [1] Tetrahedron Letters, 1986, vol. 27, # 19, p. 2099 - 2102
  • 16
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  • [ 67-56-1 ]
  • [ 5427-82-7 ]
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  • [ 1193-62-0 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 14, p. 2961 - 2964
  • 17
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Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 15, p. 2663 - 2669
  • 18
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Reference: [1] Patent: US2001/47006, 2001, A1,
[2] Patent: US2002/6943, 2002, A1,
  • 19
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Reference: [1] Patent: US2003/80320, 2003, A1,
  • 20
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Reference: [1] Canadian Journal of Chemistry, 1990, vol. 68, # 8, p. 1305 - 1308
  • 21
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Reference: [1] Patent: US4675186, 1987, A,
  • 22
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Reference: [1] Liebigs Annalen der Chemie, 1981, # 6, p. 1073 - 1088
  • 23
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Reference: [1] Liebigs Annalen der Chemie, 1981, # 6, p. 1073 - 1088
  • 24
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Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 15, p. 2663 - 2669
  • 25
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Reference: [1] Tetrahedron, 2002, vol. 58, # 33, p. 6713 - 6722
  • 26
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Reference: [1] Synthesis, 2001, # 15, p. 2281 - 2288
  • 27
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Reference: [1] Liebigs Annalen der Chemie, 1981, # 6, p. 1073 - 1088
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Reference: [1] Canadian Journal of Chemistry, 1990, vol. 68, # 8, p. 1305 - 1308
  • 29
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 21, p. 5796 - 5800
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Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 31, p. 4150 - 4152
  • 31
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Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 14, p. 2589 - 2592
  • 32
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Reference: [1] Acta Chemica Scandinavica (1947-1973), 1952, vol. 6, p. 867,872
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Reference: [1] Tetrahedron Letters, 1988, vol. 29, # 38, p. 4823 - 4826
  • 34
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Reference: [1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 1, p. 87 - 91
  • 35
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Reference: [1] Chemische Berichte, 1911, vol. 44, p. 3168
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 8, p. 1833 - 1836
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 8, p. 1833 - 1836
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Reference: [1] Acta Chemica Scandinavica (1947-1973), 1952, vol. 6, p. 867,872
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 8, p. 1833 - 1836
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 8, p. 1833 - 1836
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  • [ 1757-29-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 8, p. 1833 - 1836
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 8, p. 1833 - 1836
  • 41
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  • [ 68-12-2 ]
  • [ 1197-13-3 ]
YieldReaction ConditionsOperation in experiment
66% With trichlorophosphate In 1,2-dichloro-ethane at 0 - 20℃; for 0.25 h; Heating / reflux Anhydrous DMF (7.0 mL, 90.4 mmol) was cooled to 5-10 degrees Centigrade under nitrogen. POCl3 (7.8 mL, 83.7 mmol) was added dropwise to the cooled DMF over a couple of minutes. Dry 1,2-dichloroethane (25 mL) was then added and the solution was cooled to 0-5 degrees Centigrade during the addition of 2 (9.46 g, 75.6 mmol) in dry 1,2-dichloroethane (25 mL). The mixture was then heated to reflux for 15 minutes. The reaction was cooled to room temperature, treated with a mixture of ethyl acetate (60 mL) and water (75 mL), poured into saturated NaHCO3 (350 mL), and separated. The aqueous layer was washed three times with ether, and the combined organic extracts were washed twice with aqueous saturated Na2CO3, dried over Na2SO4, and evaporated under vacuum. The resulting solid was sublimed under reduced pressure (20?10?3 torr) at 60 degrees Centigrade in 3-hour intervals to yield compound 3 (7.79 g, 50.1 mmol, 66percent). 1H-NMR (CDCl3): ? 10.57 (br s, 1H), 9.70 (s, 1H), 6.95 (m, 2H), 3.94 (s, 3H).
63% With trichlorophosphate In dichloromethane; N,N-dimethyl-formamide at 0℃; for 4 h; Inert atmosphere; Reflux Phosphorylchloride (4.39 mmol, 0.4 mL) was added dropwise to 0.34 mLDMF at 0 C. The reaction was allowed to reach room temperatureand 2.2 mL of dry CH2Cl2 were subsequently added. The mixturewas cooled again to 0 C and a solution of 6 (500 mg, 4 mmol)was added dropwise within 1 h. The reaction mixture was thenrefluxed for 4 h, cooled to 0 C and hydrolysed with a solution ofsodium acetate (1.8 g, 22 mmol) in water (5.5 mL). The phaseswere separated and the aqueous phase was extracted with ethylacetate. The combined organic extracts were dried with Na2SO4and concentrated. The residue was purified by flash chromatography(eluent; hexane/ethyl acetate = 5/1) to afford 387 mg of compound7 (yield = 63percent). Characterization was in agreement withliterature data.17 1H NMR (500 MHz, DMSO-d6) d 13.07 (s, 1H),9.70 (s, 1H), 6.97 (d, J = 3.9 Hz, 1H), 6.90 (d, J = 3.9 Hz, 1H), 3.83(s, 3H).
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 20, p. 2997 - 3003
[2] Journal of Organic Chemistry, 2017, vol. 82, # 18, p. 9350 - 9359
[3] Patent: US6696575, 2004, B2, . Location in patent: Page column 3;4;17;18;11-12
[4] Chemical Communications, 1999, # 9, p. 843 - 844
[5] European Journal of Organic Chemistry, 1999, # 9, p. 2397 - 2403
[6] Chemistry - A European Journal, 2000, vol. 6, # 4, p. 709 - 718
[7] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 5, p. 1622 - 1629
[8] Patent: US2012/184521, 2012, A1, . Location in patent: Page/Page column 27
[9] Tetrahedron Letters, 2016, vol. 57, # 32, p. 3629 - 3634
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YieldReaction ConditionsOperation in experiment
48.18% at 0 - 20℃; To the stirred solution of methyl 1H-pyrrole-2-carboxylate (0.9 g, 7.19 mmol) in DMF (4.2 g, 57.52 mmol) at 0 00, POOl3 (5.5 g, 35.96 mmol) was added. The reaction mixture was stirred at 10 00 for 30 mm at room temperature over night. The reaction mixture was quenched with sodium hydroxide solution and extracted using ethyl acetate dried over anhydrous Na2SO4. The crude mixture of products was purified by column chromatography to yield the title compound polar spot (0.53 g, 48.18percent) as a pale yellow solid. LCMS: (M-H) = 152.1; 1H NMR: (DMSO-d6, 300MHz) 6 12.73 (5, 1H), 7.76 (5, 1H), 7.82-7.83 (d, 1H), 7.14 (5, 2H), 3.81 (5, 3H). Intermediate 12a: Methyl 5-formyl-1H-pyrrole-2-carboxylate was formed along with11 a. Upon separation of 11 a and 1 2a, intermediate 1 2a obtained (0.5 g, 45.45percent) asa pale yellow solid. LOMS: (M-H) = 152.1
Reference: [1] Tetrahedron, 1992, vol. 48, # 8, p. 1457 - 1464
[2] Tetrahedron, 2001, vol. 57, # 15, p. 3063 - 3067
[3] European Journal of Organic Chemistry, 2008, # 2, p. 324 - 329
[4] Patent: WO2014/202580, 2014, A1, . Location in patent: Page/Page column 84; 85
[5] Tetrahedron Letters, 2006, vol. 47, # 27, p. 4631 - 4634
[6] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 11, p. 2935 - 2937
[7] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5763 - 5773
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Reference: [1] Patent: EP1568698, 2005, A1, . Location in patent: Page/Page column 45-46
[2] Patent: WO2008/89453, 2008, A2, . Location in patent: Page/Page column 94-95
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Reference: [1] Organic Process Research and Development, 2018,
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Reference: [1] Organic Letters, 2010, vol. 12, # 21, p. 4872 - 4875
  • 46
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YieldReaction ConditionsOperation in experiment
84%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Inert atmosphere
Stage #2: With O-(2,4-dinitrophenyl)hydroxylamine In N,N-dimethyl-formamide; mineral oil at 0℃;
(Step 1) methy 1-amino-1H-pyrrolo-2-carboxylate; To a mixture of NaH (60percent, 4.1 g, 102.2 mmol) suspended in dimethylformamide (120 mL) at 0° C. under nitrogen atmosphere, methyl pyrrolo-1-H-2-carboxylate (8.0 g, 63.9 mmol) was slowly added over minutes. After stirring for 1 hour, a solution of 2,4-dinitrophenolamine (19.1 g, 95.9 mmol) in dimethylformamide (30 mL) was added dropwise for 30 minutes. The resulting reaction mixture was stirred at 0° C. for 2.5 hours. The reaction was completed by slowly adding saturated sodium thiosulfate aqueous solution. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with 10percent lithium chloride aqueous solution, dried with sodium sulfate, and then filtered. The filtrate was concentrated. The resulting brown residue was purified by silica gel chromatography (10percent ethyl acetate in hexane) to give the target compound as an oil (7.5 g, 53.5 mmol, 84percent yield).1H NMR (400 MHz, CDCl3): 6.96 (t, J=2.4 Hz, 1H), 6.83 (dd, J=4.4 Hz, 2.0 Hz, 1H), 6.02 (dd, J=4.4 Hz, 2.8 Hz, 1H) 5.54 (br s, 2H), 3.83 (s, 3H).
81.1%
Stage #1: With sodium hydride In hexanes; N,N-dimethyl-formamide at -5℃; Inert atmosphere
Stage #2: With diphenyl aminooxyphosphonate In hexanes; N,N-dimethyl-formamide at 20℃; for 4 h;
Stage #3: With sodium thiosulfate In hexanes; water; N,N-dimethyl-formamide at 80℃; for 1 h;
a) Methyl 1 -amino-1 W-pyrrole-2-carboxylateSodium hydride (4.40 g, 0.1 1 mol, 60percent in hexanes) was suspended in DMF (550 ml) under nitrogen atmosphere. Once cooled at - 5°C, methyl 1 H-pyrrole-2-carboxylate (1 1 .0 g, 0.09 mol) dissolved in DMF (182 ml) was dropwise added and vigorously stirred for 30. 277ml more of DMF was added and then O- (diphenylphosphoryl)hydroxylamine (32.8g, 0.14 mol) was introduced into the reaction mixture. The reaction mixture was stirred at room temperature for 4h. Once the reaction is over, 11 of saturated sodium thiosulfate solution (x5H20) was added and the mixture was warmed to 80°C for 1 h. Once at room temperature, 11 of ethyl ether was added and the phases separated. The aqueous phase was twice extracted with ethyl ether. The organic phase was washed with water and brine, dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. 10.41 g (81 .1 percent yield) of the final compound were obtained.LRMS (m/z): 141 (M+1 )+
Reference: [1] Patent: US2011/183983, 2011, A1, . Location in patent: Page/Page column 32
[2] Patent: WO2012/146666, 2012, A1, . Location in patent: Page/Page column 172
[3] Patent: US2010/47367, 2010, A1, . Location in patent: Page/Page column 22
[4] Patent: WO2010/71885, 2010, A1, . Location in patent: Page/Page column 335
[5] Patent: WO2016/144848, 2016, A1, . Location in patent: Page/Page column 33
[6] Patent: CN105524068, 2016, A, . Location in patent: Paragraph 0171; 0173
  • 47
  • [ 1193-62-0 ]
  • [ 263382-27-0 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 14, p. 2589 - 2592
[2] Chemistry - A European Journal, 2000, vol. 6, # 4, p. 709 - 718
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