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CAS No. :630120-99-9 MDL No. :MFCD11874623
Formula : C12H10BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :KKCMCYRLJVVNTQ-UHFFFAOYSA-N
M.W : 264.12 Pubchem ID :16094696
Synonyms :

Safety of [ 630120-99-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 630120-99-9 ]

* 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 [ 630120-99-9 ]
  • Downstream synthetic route of [ 630120-99-9 ]

[ 630120-99-9 ] Synthesis Path-Upstream   1~7

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  • [ 55717-45-8 ]
  • [ 100-51-6 ]
  • [ 630120-99-9 ]
YieldReaction ConditionsOperation in experiment
66% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 35℃; for 18 h; To a 1L round bottom flask equipped with a large stir bar was added 6- bromopyridin-3-ol (24.69 g, 142 mmol), benzyl alcohol (15.42 mL, 149 mmol), triphenylphosphine (39.1 g, 149 mmol) and THF (600 mL). The flask was placed in a r.t.water bath. To the stirred solution was added in six portions DIAD (29.0 mL, 149 mmol). The internal temperature increased from 20 deg to 35 deg C, and was 35 deg C at the completion of the addition. After stirring for 18 h the reaction solution was concentrated in vacuo to afford a liquid residue. The material was diluted with hexane: Et20 (1:1, 850 mL). A precipitate was immediately formed. The mixture was stirred for 5 minutes, then the liquid was decanted and reserved. The solids were treated with Et20 (200 mL), and the mixture was stirred for 5 minutes. The solution was diluted with hexanes (200 mL), and the mixture was then stirred for 5 minutes. The mixture and the reserved solution were combined and filtered through a fine-fritted vacuum funnel. The filtrate wasconcentrated in vacuo. The resulting residue was diluted with a small amount of acetone and then concentrated onto Celite in vacuo. The resulting powder was subjected to Si02 chromatography (330g Si02 column, hexanes:EtOAc 100:0 - 80:20) to afford 5- (benzyloxy)-2-bromopyridine as a colorless, crystalline solid (24.84 g, 66percent). ‘H NMR (400 MHz, CHLOROFORM-d) 8.16 (d, J=3.2 Hz, 1H), 7.45 - 7.36 (m, 6H), 7.18 (dd,J=8.6, 3.2 Hz, 1H), 5.12 (s, 2H).
Reference: [1] Patent: WO2018/127800, 2018, A1, . Location in patent: Page/Page column 71; 72
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1370 - 1387
[3] Patent: WO2009/140163, 2009, A1, . Location in patent: Page/Page column 37
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  • [ 55717-45-8 ]
  • [ 100-39-0 ]
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YieldReaction ConditionsOperation in experiment
96.7% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 6 h; Example 14a) 5-Benzyloxy-2-bromo-pyridineJTTo a solution of 10.0 g (57.47 mmol) of 2-bromo-5-hydroxypyridine in 400 mL DMF was added 14.75 g (86.21 mmol) of benzyl bromide and 23.82 g (172.4 mmol) of potassium carbonate. The mixture was stirred for 6 h at 600C and overnight at room temperature. The suspension was filtered off and after evaporation of the solvent the residue was chromatogra- phed on silica gel using a dichloromethane/methanol gradient. Yield: 14.82 g (96.7 percent).MS (ESIpos): m/z = 264, 266 [M+H]+ 1H-NMR (300MHz, CHLOROFORM-d): δ [ppm]= 5.10 (s, 2H), 7.16 (dd, 1 H), 7.32 - 7.47 (m, 6H), 8.14 (d, 1 H).
96.7% at 20 - 60℃; Example 1N-(2-{4-[5-(benzyloxy)pyridin-2-yl]piperazin-1 -yl}-2-oxoethyl)-2-iodopyridine-4-carboxamide -Benzyloxy-2-bromo-pyridineTo a solution of 1 0.0 g (57.47 m mol) of 2-bromo-5-hydroxypyridine in 400 ml. N,N- dimethylformamide (DMF) was added 14.75 g (86.21 mmol) of benzyl bromide and 23.82 g (172.4 mmol) of potassium carbonate. The mixture was stirred for 6 h at 60 C and overnight at room temperature. The suspension was filtered off and after evaporation of the solvent the residue was chromatographed on silica gel using a dichloromethane/methanol gradient. Yield: 14.82 g (96.7 percent).MS (ESIpos): m/z = 264, 266 [M+H]+1H-NMR (300MHz, CHLOROFORM-d): d [ppm]6H), 8.14 (d, 1 H).
96.7% With potassium carbonate In N,N-dimethyl-formamide at 20 - 60℃; -Benzyloxy-2-bromo-pyridineTo a solution of 1 0.0 g (57.47 mmol) of 2-bromo-5-hydroxypyridine in 400 mL N,N- dimethylformamide (DMF) was added 14.75 g (86.21 mmol) of benzyl bromide and 23.82 g (172.4 mmol) of potassium carbonate. The mixture was stirred for 6 h at 60°C and overnight at room temperature. The suspension was filtered off and after evaporation of the solvent the residue was chromatographed on silica gel using a dichloromethane/methanol gradient. Yield: 14.82 g (96.7 percent). MS (ESIpos): m/z = 264, 266 [M+H]+ 1H-NMR (300MHz, CHLOROFORM-d): δ [ppm]6H), 8.14 (d, 1 H).
92% With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1 h; Cooling with ice Compound (II-3) (5.00 g, 28.7 mmol) was dissolved in DMF (30 mL), potassium carbonate (7.94 g, 57.5 mmol),benzyl bromide (4.1 mL, 35 mmol) and TBAI (531 mg, 1.44 mmol) were added under ice-cooling, and the mixture waswarmed to room temperature and stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extractedwith ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydroussodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified by silica gelcolumn chromatography (n-hexane:ethyl acetate = 97:3 →80:20) to give compound (M-16) (yield 6.97 g, 92percent) as awhite solid
92% With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1 h; Cooling with ice Compound (II-3) (5.00 g, 28.7 mmol) was dissolved in DMF (30 mL), And potassium carbonate (7.94 g, 57.5 mmol),Benzyl bromide (4.1 mL, 35 mmol) and TBAI (531 mg, 1.44 mmol) were added under ice cooling,The temperature was raised to room temperature and stirred for 1 hour.Water was added to the reaction solution, and the mixture was extracted with ethyl acetate.The organic layer was washed successively with water and saturated brine,Dried over anhydrous sodium sulfate, and filtered.The solvent was distilled off under reduced pressure.The residue was purified by silica gel column chromatography(n-hexane: ethyl acetate = 97: 3 -> 80: 20)To obtain compound (M-16)(Yield 6.97 g, Yield 92percent)As a white solid.
89% With caesium carbonate In acetonitrile at 20℃; for 3 h; 6-Bromopyridin-3-ol (3.00 g, 17.24 mmol) and cesium carbonate (8.43 g, 25.9 mmol) were stirred in dry acetonitrile (30 mL). Benzyl bromide (3. 24 g, 18.97 mmol) was added and stirred at RT for 3 h. After completion of reaction, the reaction mixture was filtered and washed with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to give the title compound, 5-(benzyloxy)-2-bromopyridine. Yield: 4.05g, 89percent.
89% With caesium carbonate In acetonitrile at 20℃; A mixture of benzylbromide (3.24g, 18.97mmol), 6-bromopyridin-3-ol (3g, 17.24mmol) and cesium carbonate (8.43 g, 25.90 mmol) in dry acetonitrile (50 mL) was stirred overnight at room temperature. After the completion of the reaction, the reaction mixture was diluted with ethyl acetate (80 mL) and filtered. The filtrate was concentrated under vacuum to afford the title compound (4.05 g). Yield: 89percent JH NMR (300 MHz, CDCI3): δ 8.15 (s, 1H), 7.42-7.37 (m, 5H), 7.19-7.15 (m, 1H), 5.11 (s, 2H).
86% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2 h; To a solution of 6-bromopyridin-3-ol (2 g, 11.49 mmol, 1 eq) in N,N- dimethylformamide (20 mL) was added potassium carbonate (3.18 g, 22.99 mmol, 2 eq) and benzyl bromide (2.16 g, 12.64 mmol, 1.5 mL, 1.1 eq). The mixture was stirred at 20 °C for 2 hours. Thin layer chromatography (petroleum ether : ethyl acetate = 3: 1) indicated the starting material was consumed completely and one new spot formed. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (20 mL x 3). The combined organic layers were washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether : ethyl acetate = 1:0 to 50: 1). Compound 5-benzyloxy-2-bromo-pyridine (2.6 g, 9.84 mmol, 86percent yield) was obtained as a white solid. 1H NMR (400 MHz, CDCI3- ) δ 8.14 (d, J=3.2 Hz, 1H), 7.46 - 7.31 (m, 6H), 7.16 (dd, J=3.2, 8.8 Hz, 1H), 5.10 (s, 2H).
85% With potassium carbonate In acetone at 70℃; for 2 h; Step 1:To a solution of 2-Bromo 5-hydroxypyridine (5g, 29 mmol) in acetone (100 mL), is added K2CO3 (7.9 g, 58 mmoL) followed by benzyl bromide (5.1 mL, 43 mmol).The resulting suspension is heated at 70 0C for 2 hours. The solution is then diluted with water, and the acetone removed in vacuo. The aqueous phase is extracted with ethyl acetate, and the combined organic extracts are washed with brine, dried overNa2SO4 and concentrated in vacuo. The resulting residue is purified on silica with hexanes/ethyl acetate as the eluent, 6.4g, 85percent, LC/MS ESI m/z (M+H)+ = 266.3.
83% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 13 h; Cooling with ice Step 11-1 2-Bromo-5-hydroxypyridine (5.8 g), N,N-dimethylformamide (58 ml) and potassium carbonate (5.1 g) were mixed, benzyl bromide (4.4 ml) was added under ice-cooling and the mixture was stirred at room temperature for 13 hr. To the reaction mixture were added ethyl acetate (58 ml) and water (87 ml) and the organic layer was separated from the mixture and washed successively with water (60 ml, 30 ml) twice and with saturated brine (30 ml). The organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (eluent: hexane/ethyl acetate=10/1-7/1) to give the compound described in the above-mentioned scheme (7.4 g, 83percent).1H-NMR (CDCl3) δ: 5.09 (s, 2H), 7.15 (dd, 1H, J=8.1, 3.2 Hz), 7.33-7.38 (m, 1H), 7.36 (d, 1H, J=8.1 Hz), 7.40-7.41 (m, 4H), 8.13 (d, 1H, J=3.2 Hz).
80% With caesium carbonate In acetonitrile at 20℃; To 6-bromopyridin-3-ol (10 g, 57.5 mmol) and cesium carbonate (28.1 g, 86 mmol) in acetonitrile (50 mL), benzyl bromide (8.20 mL, 69.0 mmol) was added and the reaction mass was allowed to stir at room temperature overnight. The reaction mass was quenched with water and extracted with ethyl acetate (2 x 100 mL), organic layer was dried over sodium sulphate and concentrated to give crude mass which was purified using column chromatography to provide 5-(benzyloxy)-2-bromopyridine (12.3 g, 46.1 mmol, 80percent yield). *H NMR (300 MHz, CDCI3) : δ 8.19 (d, J = 1.5 Hz, 1 H), 7.55 (d, J = 8.7 Hz, 1 H), 7.47- 7.32 (m, 6 H), 5.18 (s, 2 H); LCMS (m/z): 265 (M + l).
79%
Stage #1: With sodium hydride In tetrahydrofuran at 0 - 25℃; for 1 h;
Stage #2: at 18 - 25℃;
To a suspension of NaH (60percent in oil, 0.28 g, 6.9 mmol) in THF (6.0 ml) was added 6-bromopyridin-3-ol (1.0 g, 5.8 mmol) at 0 °C. The mixture was stirred at 0 °C for 30 min and at room temperature for additional 30 min. To this mixture was added a solution OF BENZYLBROMIDE (1. 1 g, 6.3 mmol) in DMSO (6.0 ml) slowly at room temperature and the mixture was stirred at room temperature overnight. Sat. NAH2PO4 aq. was slowly added to the mixture and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (10 ml x 3). The combined extracts were washed with brine, dried over MGS04, and evaporated in vacuum. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 50: 1 as eluent) to afford the titled compound as colorless oil. (1.2 g, 79percent) APOS;H NMR (DMSO-d6) 8 : 8.20 (d, J = 2.9 Hz, 1H), 7.56 (d, J = 8.8 Hz, 1H), 7.50-7. 32 (m, 6H), 5.19 (s, 2H) ppm.
79% With potassium carbonate In acetone at 80℃; for 3 h; To a stirred solution of 6-bromopyridin-3-ol (100 g, 575 mmol), K2C03 (119 g, 862 mmol) in acetone (1 L) was added benzyl bromide (0.075 L, 632 mmol). The mxiture was stirred for 3 h at 80 °C. LCMS showed completion of reaction. Then, the mixture was cooled to 20 °C and poured into water (250 mL). Theprecipitate was filtered, taken up in in DCM and washed with sat. NaHCO3 (50 mL), water (50 mL), brine (50 mL) and concentrated to afford 5-(benzyloxy)-2-bromopyridine (120 g, 454 mmol, 79 percent yield) as a off-white solid.
72%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.333333 h; Inert atmosphere
Stage #2: at 0 - 20℃;
2-Bromo-5-hydroxypyridine (347 mg, 2 mmol) in DMF (3 ml.) was added dropwise over a period of 10min to a suspension of NaH (88 mg, 2.3 mmol) in DMF (2 mL) at O0C under Ar(g). The reaction mixture was then stirred at rt for 10min, after which it was again cooled down at O0C, and benzyl bromide (0.25 mL, 2.1 mmol) was added. The reaction mixture was stirred at rt for 2.5h, after which it was poured onto brine (20 mL) and EtOAc (20 mL) was added. The phases were separated and the aqueous phase was extracted with EtOAc (20 mL). The organic phases were combined, dried over MgSO4, filtered and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with hexane/EtOAc (95:5 to 90:10) to furnish I as a colourless oil (380 mg, 72percent).1H NMR (400MHz, CDCI3) δH: 8.14 (d, J=3.5Hz, 1 H), 7.46-7.29 (m, 6H), 7.16 (dd, J=3.3, 8.8Hz, 1 H), 5.10 (s, 2H). MW: 264.12. LCMS (ES): found 265.0 [MH]+.
66%
Stage #1: With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 16 h;
To a stirred solution of 6-bromopyridin-3-ol (500 mg, 2.87 mmol) in DMF (10 mL), KOH (482 mg, 8.61mmol) was added at rt. The resulting mixture was stirred for 15 min at rt and then, benzyl bromide (737 mg, 4.31mmol) was added at 0 "C. The resulting solution was stirred at rt for 16h. Then, it was diluted with water (100mL), and extracted with EtOAc (2 x 200 mL). The combined organic layers were dried over Na2S04 andconcentrated. The crude compound was purified by flash column chromatography and eluted with 15percent EtOAc/pet ether to obtain the title compound (0.5 g, 66percent) as an off white color solid. LC-MS (method 23): Rt = 1.92 min; m/z = 265.95 (M+H++2).
64%
Stage #1: With sodium hydride In N,N-dimethyl-formamide for 0.5 h;
Stage #2: at 20℃; for 16 - 24 h;
2-Bromo-5-hydroxypyridine (2 mmol) is dissolved in DMF (2.5 ml) and NaH (1.4 eq., 60percent suspension in liquid paraffin) is added. After 30 min, benzylbromide (1.1 eq.) is added and the reaction stirred 16 h at RT. The reaction solution is diluted with water and extracted with methyl tert- butyl ether. The combined organic layers are dried over Na2SO4 and the solvent removed in vacuo. 5-Benzyloxy-2-bromo-pyridine is obtained after column chromatography (heptan/ethyl acetate) as a colourless powder in a yield of 64 percent; HPLC (method C): 2.09 min; LC-MS (method A): 1.987 min, 263.95 (M+H+).; 2-Bromo-5-hydroxypyridine (3 mmol) is dissolved in DMF (2.5 ml) and NaH (1.4 eq., 60percent suspension in liquid paraffin) is added. After 30 min I ,- benzylbromide (1.1 eq.) is added and the reaction solution is stirred 24 hours. The reaction solution is pored into water and extracted with methyl- tert.-butyl ether. The combined organic layers are dried over Na2SO4 and the solvent is removed in vacuo. 5-Benzyloxy-2-bromo-pyridine is obtained after column chromatography as brown oil in a yield of 80 percent. HPLC20(method C): 2.01 min; LC-MS (method A): 1.97 min, 264.00 (MH+).

Reference: [1] Patent: WO2010/28776, 2010, A1, . Location in patent: Page/Page column 75
[2] Patent: WO2011/95593, 2011, A1, . Location in patent: Page/Page column 9
[3] Patent: WO2011/110511, 2011, A1, . Location in patent: Page/Page column 21-22
[4] Organic Letters, 2013, vol. 15, # 1, p. 140 - 143
[5] Patent: EP3351533, 2018, A1, . Location in patent: Paragraph 0338; 0339
[6] Patent: JP2018/145180, 2018, A, . Location in patent: Paragraph 0326; 0327; 0328
[7] Patent: WO2015/125085, 2015, A1, . Location in patent: Page/Page column 97
[8] Patent: WO2016/12965, 2016, A2, . Location in patent: Page/Page column 87; 99-100; 102-103
[9] Patent: WO2018/140809, 2018, A1, . Location in patent: Paragraph 00479; 00690; 00691; 00692
[10] Patent: WO2010/56585, 2010, A2, . Location in patent: Page/Page column 72
[11] Patent: US2011/77267, 2011, A1, . Location in patent: Page/Page column 46
[12] Patent: WO2016/125182, 2016, A1, . Location in patent: Page/Page column 48
[13] Patent: WO2004/54579, 2004, A1, . Location in patent: Page/Page column 78
[14] Patent: WO2018/127800, 2018, A1, . Location in patent: Page/Page column 72
[15] Patent: WO2010/86646, 2010, A1, . Location in patent: Page/Page column 37
[16] Patent: WO2017/207813, 2017, A1, . Location in patent: Page/Page column 94
[17] Patent: WO2009/46784, 2009, A1, . Location in patent: Page/Page column 57; 76
[18] Patent: WO2009/38974, 2009, A1, . Location in patent: Page/Page column 94-95
[19] Journal of Medicinal Chemistry, 2008, vol. 51, # 18, p. 5766 - 5779
[20] Patent: EP2149550, 2010, A1, . Location in patent: Page/Page column 83
[21] Patent: WO2012/123311, 2012, A1, . Location in patent: Page/Page column 65
[22] Patent: US2012/232061, 2012, A1, . Location in patent: Page/Page column 37
[23] Patent: WO2016/196879, 2016, A1, . Location in patent: Paragraph 000570; 000571
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Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 25, p. 7450 - 7465
[2] Patent: US2003/229094, 2003, A1, . Location in patent: Page 113
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Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 2, p. 863 - 872
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Reference: [1] Heterocycles, 2011, vol. 83, # 9, p. 1989 - 2000
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Reference: [1] Patent: US2004/29887, 2004, A1,
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Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 25, p. 7450 - 7465
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