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[ CAS No. 78607-36-0 ]

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CAS No. :78607-36-0 MDL No. :MFCD00661298
Formula : C5H3ClIN Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :239.44 g/mol Pubchem ID :2735743
Synonyms :

Safety of [ 78607-36-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 78607-36-0 ]

  • Upstream synthesis route of [ 78607-36-0 ]
  • Downstream synthetic route of [ 78607-36-0 ]

[ 78607-36-0 ] Synthesis Path-Upstream   1~30

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YieldReaction ConditionsOperation in experiment
95% With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 3 h; A solution of 2-chloro-3-iodopyridine (12 g, 50 mmol) in 20 ML of THF was slowly added to a cold (-78°C) lithium diisopropylamide solution (prepared by the addition of n- butyllithium 1.6 M (31.25 ML, 50 mmol) in hexanes to a solution of diisopropylamine (7 mL, 50 mmol) in THF (100 mL). After 3h, water (20 mL) was added to the mixture, which was extracted with ether (2 x 100 mL). The organic layers were dried over magnesium sulfate, filtered and concentrated under vacuum (20°C) to afford a brown solid, which was purified by filtration over silica (ethyl acetate/heptane 8/2). Yield: 95percent (11.4 g), pale yellow NEEDLES. IH NMR (CDC13) : 8 8.07 (d, J = 5.3 Hz, 1H), 7.76 (d, J = 1.1 Hz, 1H), 7.59 (dd, J = 5. 0/1. 1 Hz, 1H). 13C NMR (CDC13) : 8 151.7, 149.6, 133. 0,131. 5,106. 6. MS (EI) m/z 240 (M+1).
80% With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - -15℃; for 1.33333 h; To a THF solution (40 ml) of Diisopropyl amine (4.46 ml, 1.5 eqv) was added BuLi (1.88 M, 1.5 eqv) at -15° C. and the resulting reaction mixture was allowed to stir at same temperature for 20 minutes. It was then cooled to -78° C. and 2-chloro-3-iodopyridine (5 g, 20.92 mmol) in THF (10 ml) was added dropwise at the same temperature and allowed to stir for 1 hr at -78° C. Reaction was quenched with water (10 ml), stirred at ambient temperature for 15 minutes and extracted with ethyl acetate. Organic layer was washed successively with brine and finally dried over sodium sulfate. Evaporation of organic layer under reduced pressure gave the crude product which was immediately used in the next step without any further purification. Yield: 80percent (Crude)
75%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - -5℃; for 2 h;
Stage #2: With water In tetrahydrofuran for 0.25 h;
Preparation of amine unit A4 1. A solution of diisopropylamine (12.7 g) in THF (160 ml) was cooled to -15° C., and n-BuLi (83 ml) was added dropwise over a period of 20 min at -10° C. After stirring for 20 min at -5° C., the reaction mixture was cooled to -78° C., and 2-chloro-3-iodo-pyridine (20 g) dissolved in THF (40 ml) was added dropwise over a period of 20 min. The reaction mixture was stirred for 1 h at -78° C. After addition of water (40 ml), stirring was carried out for 15 min. The organic phase was separated off and dried over Na2SO4. After filtration, the solvent was removed in vacuo and the residue was purified by flash chromatography (silica, 5percent ethyl acetate/n-hexane). Yield: 15 g (75percent)
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1397 - 1401
[2] Patent: WO2004/52880, 2004, A1, . Location in patent: Page 30
[3] Patent: US2009/186899, 2009, A1, . Location in patent: Page/Page column 45-46
[4] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
[5] Patent: US2008/249128, 2008, A1, . Location in patent: Page/Page column 46
[6] Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7832 - 7838
[7] Patent: WO2009/90055, 2009, A1, . Location in patent: Page/Page column 133; 134
[8] Patent: US2009/264400, 2009, A1, . Location in patent: Page/Page column 64
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Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 42, p. 7873 - 7877
[2] ChemPhysChem, 2016, vol. 17, # 24, p. 4090 - 4101
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Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 47, p. 13284 - 13297
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Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 47, p. 13284 - 13297
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Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 47, p. 13284 - 13297
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Reference: [1] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
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  • [ 104830-06-0 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1985, vol. 33, # 11, p. 4764 - 4768
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 41, p. 7564 - 7567
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  • [ 65753-47-1 ]
Reference: [1] European Journal of Organic Chemistry, 2002, # 2, p. 327 - 330
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  • [ 65753-47-1 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 79, p. 75465 - 75469
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YieldReaction ConditionsOperation in experiment
72%
Stage #1: With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 2 h;
Stage #2: With iodine In tetrahydrofuran; hexanes for 0.5 h;
2,2, 6,6-tetramethylpiperidine (17 ML, 14 g, 0.1 mol) and 2-chloropyridine (9.5 mL, 11.5 g, 0.1 mol) were consecutively added at-78°C to n-butyllithium 1.6 M in hexanes (62.5 mL, 0.1 mol) in 150 mL of tetrahydrofuran. After 2h AT-78°C, the mixture was treated with a solution of iodine (25.5 g, 0.1 mol) in THF (50 ML) and stirred for 30 min before being partitioned between water (100 mL) and diethyl ether (3 x 50 mL). The combined organic layers were washed with a saturated aqueous solution of sodium thiosulfate (2 x 50 mL), dried over magnesium sulfate, filtered and concentrated under vacuum to afford a crude solid which was purified by flash chromatography (heptane/ethyl acetate 90/10). Yield: 72percent (17.3 g), yellow SOLID. IH NMR (CDC13) : 8 8.38 (dd, J = 4.6/1. 7 Hz, 1H), 8.16 (dd, J = 8. 0/1. 6 Hz, 1H), 6.96 (dd, J = 8.0/4. 6 Hz, 1H). 13C NMR (CDC13) : 8 154.5, 148.9, 148 : 8, 123.2, 94.9. MS (EI) M/Z 240 (M+1).
Reference: [1] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1397 - 1401
[3] Patent: WO2004/52880, 2004, A1, . Location in patent: Page 29-30
[4] Tetrahedron Letters, 1994, vol. 35, # 35, p. 6489 - 6492
[5] Organic letters, 2002, vol. 4, # 13, p. 2201 - 2203
[6] Angewandte Chemie - International Edition, 2018, vol. 57, # 33, p. 10748 - 10751[7] Angew. Chem., 2018, vol. 130, # 33, p. 10908 - 10911,4
[8] Chemistry - A European Journal, 2009, vol. 15, # 39, p. 10280 - 10290
[9] Journal of Organometallic Chemistry, 1991, vol. 406, # 1+2, p. 49 - 56
[10] Tetrahedron, 1993, vol. 49, # 1, p. 49 - 64
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Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7752 - 7754
[2] Synthesis, 2007, # 1, p. 81 - 84
[3] Tetrahedron Letters, 2009, vol. 50, # 52, p. 7263 - 7267
[4] Chemical & Pharmaceutical Bulletin, 1985, vol. 33, # 11, p. 4764 - 4768
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Reference: [1] Patent: US2007/60618, 2007, A1, . Location in patent: Page/Page column 17
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Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 42, p. 7873 - 7877
[2] ChemPhysChem, 2016, vol. 17, # 24, p. 4090 - 4101
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Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 47, p. 13284 - 13297
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Reference: [1] Advanced Synthesis and Catalysis, 2011, vol. 353, # 8, p. 1359 - 1366
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Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 47, p. 13284 - 13297
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Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 47, p. 13284 - 13297
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YieldReaction ConditionsOperation in experiment
65% With cesium fluoride In dimethyl sulfoxide at 130℃; for 4 h; General procedure: To a solution of 2,3-dichloropyridine(1.00 g, 6.76 mmol) in DMSO (33.8 ml) was added CsF (2.053 g, 13.51mmol) at room temperature. The mixture was stirred at 110 °C under air for 20h. The mixture was quenched with water at room temperature and extracted withEtOAc. The organic layer was separated, washed with water and brine, dried overNa2SO4 and concentrated in vacuo. The residue waspurified by column chromatography (silica gel, eluted with EtOAc in hexane) togive 3-chloro-2-fluoropyridine (0.639 g, 4.86 mmol, 71.9 percent) as colorlessoil. Thecompound 3B'-8B' were prepared in amanner similar to that described for 2B'.
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 44, p. 6043 - 6046
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Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7832 - 7838
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YieldReaction ConditionsOperation in experiment
54%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 3 h;
Stage #2: at -78℃; for 1.5 h;
Example 1 :N-(2-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl)cyclopropanecarboxamideStep 1 :2-Chloro-4-iodonicotinaldehydeA mixture of 2-chloro-3-iodopyridine (5.0 g, 21 mmol) in dry THF (30 mL) was slowly added to a cold (-78 °C) solution of lithium diisopropylamide (15 mL, 30 mmol) in dry THF (50 mL). The resulting mixture was stirred for 3 h at this temperature. Ethyl formate (4.0 g, 54 mmol) was then added. Stirring was continued for 1.5 h at the same temperature. Water (10 mL) was added to quench the reaction, and then the resulting mixture was warmed to room temperature. 2M HC1 (50 mL) was added and then the THF was removed under reduced pressure. The aqueous residue was extracted with ethyl acetate (2 x 50 mL). The combined organic extracts were washed with brine, dried over Na2S04 and concentrated under reduced pressure. The residue was purified on silica gel (diethyl ether: petroleum ether = 1 : 4) to give the desired product 2-chloro- 4-iodonicotinaldehyde as a yellow solid (3.0 g, 54percent yield). NMR (500 MHz, CDC13): δ 10.22 (s, 1H), 8.09 (d, J = 5.0 Hz, 1H), 7.95 (d, J = 5.0 Hz, 1H).
Reference: [1] Synthetic Communications, 1996, vol. 26, # 23, p. 4421 - 4436
[2] Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7832 - 7838
[3] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 5, p. 1039 - 1044
[4] Patent: WO2012/66061, 2012, A1, . Location in patent: Page/Page column 76-77
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Reference: [1] Synthetic Communications, 1996, vol. 26, # 23, p. 4421 - 4436
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Reference: [1] Patent: US2011/152273, 2011, A1,
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Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 47, p. 13284 - 13297
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Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 47, p. 13284 - 13297
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Reference: [1] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
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Reference: [1] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
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Reference: [1] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
[2] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
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Reference: [1] Tetrahedron, 2002, vol. 58, # 17, p. 3323 - 3328
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Reference: [1] Tetrahedron, 2002, vol. 58, # 17, p. 3323 - 3328
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  • [ 411235-57-9 ]
  • [ 865664-04-6 ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 120℃; for 4 h; To a mixture of 2-chloro-3-iodopyridine (2.39 g, 9.98 mmol), cyclopropylboronic acid (860 mg, 10 mmol) and potassium carbonate (4.14 g, 30.0 mmol) in 1 ,4-dioxane (50 mL) was added tetrakis(triphenylphosphine)palladium(0) (1 .16 g, 1 .00 mmol). The reaction mixture was stirred at 120 °C for 4 hours, then diluted with ethyl acetate (50 mL) and filtered. The filtrate was concentrated and the residue was purified by silica gel chromatography (Gradient: 10percent to 30percent ethyl acetate in petroleum ether) to afford the product as a colorless oil. Yield: 1 g, 6 mmol, 60percent. 1 H NMR (400 MHz, CDCl3) δ 8.20 (dd, J=4.7, 1.8 Hz, 1 H), 7.24-7.28 (m, 1 H), 7.14 (br dd, J=7.6, 4.8 Hz, 1 H), 2.12-2.21 (m, 1 H), 1.04-1.11 (m, 2H), 0.67-0.72 (m, 2H).
Reference: [1] Patent: WO2014/207601, 2014, A1, . Location in patent: Page/Page column 70; 72
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