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[ CAS No. 53014-84-9 ]

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Chemical Structure| 53014-84-9
Chemical Structure| 53014-84-9
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CAS No. :53014-84-9 MDL No. :MFCD08272279
Formula : C7H7NO Boiling Point : 213.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :121.14 g/mol Pubchem ID :10192566
Synonyms :

Safety of [ 53014-84-9 ]

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

Application In Synthesis of [ 53014-84-9 ]

  • Upstream synthesis route of [ 53014-84-9 ]
  • Downstream synthetic route of [ 53014-84-9 ]

[ 53014-84-9 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 34107-46-5 ]
  • [ 53014-84-9 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -60℃; for 1.33333 h;
Stage #2: With triethylamine In dichloromethane at -60 - 20℃; for 0.166667 h;
B.
Preparation of 6-methylnicotinaldehyde
To a solution of oxalyl chloride (2 M in dichloromethane, 9.34 mL, 18.68 mmol) in 30 mL dichloromethane at -60° C. under argon, dimethyl sulfoxide (3.1 g, 2.81 mL, 39.63 mmol) was added over 20 min.
The mixture was stirred at -60° C. for 20 min before a solution of (6-methylpyridin-3-yl)methanol in 8 mL dichloromethane was added over 20 min.
The reaction mixture was stirred for 20 min, and then triethylamine (8.02 g, 11.05 mL, 79.25 mmol) was added over 10 min.
The reaction mixture was allowed to warm up to room temperature and 48 mL water was added.
The mixture was extracted with dichloromethane and the combined extracts were dried (Na2SO4), filtered and concentrated.
The crude product was purified by automated silica gel chromatography (eluted with ethyl acetate-hexanes) to isolate 1.67 g (85percent) of the title compound as a light brown oil. HPLC: retention time=0.19 min.
85% With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -60℃; for 1.5 h; B.
Preparation of 6-methylnicotinaldehyde
To a solution of oxalyl chloride (2 M in dichloromethane, 9.34 mL, 18.68 mmol) in 30 mL dichloromethane at -60° C. under argon, dimethyl sulfoxide (3.1 g, 2.81 mL, 39.63 mmol) was added over 20 min.
The mixture was stirred at -60° C. for 20 min before a solution of (6-methylpyridin-3-yl)methanol in 8 mL dichloromethane was added over 20 min.
The reaction mixture was stirred for 20 min, and then triethylamine (8.02 g, 11.05 mL, 79.25 mmol) was added over 10 min.
The reaction mixture was allowed to warm up to room temperature and 48 mL water was added.
The mixture was extracted with dichloromethane and the combined extracts were dried (Na2SO4), filtered and concentrated.
The crude product was purified by automated silica gel chromatography (eluted with ethyl acetate-hexanes) to isolate 1.67 g (85percent) of the title compound as a light brown oil. HPLC: retention time=0.19 min.
Reference: [1] Patent: US2006/287341, 2006, A1, . Location in patent: Page/Page column 46
[2] Patent: US2007/4772, 2007, A1, . Location in patent: Page/Page column 82
[3] Journal of Medicinal Chemistry, 1989, vol. 32, # 3, p. 583 - 593
[4] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
[5] Patent: US4778796, 1988, A,
[6] Patent: US2005/131017, 2005, A1, . Location in patent: Page/Page column 103
[7] Patent: EP210782, 1991, B1,
[8] Patent: WO2008/40934, 2008, A1, . Location in patent: Page/Page column 26-27
[9] Patent: WO2009/110985, 2009, A2, . Location in patent: Page/Page column 63
  • 2
  • [ 3430-13-5 ]
  • [ 68-12-2 ]
  • [ 53014-84-9 ]
YieldReaction ConditionsOperation in experiment
72%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at -78℃; for 1 h;
To a solution of 5-bromo-2-methylpyridine (151; 10 g, 58.1 mmol) in THF (150 mL) was added n-BuLi (2.5 M, 25.6 mL) at -78 0C. The reaction mixture was stirred at this temperature for Ih. DMF (1.30 mL) was then added and the resulting reaction mixture was stirred for 1 h at -78 °C. The reaction was quenched by the addition of aq. NH4Cl. Upon warming to room temperature, the mixture was extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography to afford 6-methylnicotinaldehyde 152 (5.0 g, 72percent).
72%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at -78℃; for 1 h;
Example 22. Synthesis of 2-(6-methylpyridin-3-yl)-N-(thiazol-2-yl)-[l,2,4]triazolo[l,5- a]pyridine-8-carboxamide (Compound 210): Step 1) Preparation of 6-methylnicotinaldehyde (93): 91To a solution of 5-bromo-2-methylpyridine (91; 10 g, 58.1 mmol) in THF (150 mL) was added n-BuLi (2.5 M, 25.6 mL) at -78 0C. The reaction mixture was stirred at this temperature for Ih. DMF (1.30 mL) was then added and the resulting reaction mixture was stirred for 1 h at -78 0C. The reaction was quenched by the addition of aq. NH4Cl. Upon warming to room temperature, the mixture was extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography to afford 6-methylnicotinaldehyde 92 (5.0 g, 72percent).
38%
Stage #1: With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane at 10℃; for 1 h;
Stage #2: at 20℃; for 2 h;
Step 1
6-Methylnicotinaldehyde:
At about 0° C. and under an atmosphere of nitrogen, n-butyllithium (2.5 M in hexane, 20 mL, 1.00 equiv) was added to a solution of isopropylmagnesiumchloride (2.0 M in tetrahydrofuran, 12.5 mL, 0.50 equiv) in tetrahydrofuran (100 mL).
The resulting solution was stirred at about 0° C. for about 30 minutes, and then 5-bromo-2-methylpyridine (8.6 g, 50 mmol, 1.00 equiv) was added.
After stirring for about 1 hour at about -10° C., dimethylformamide (14.6 g, 200 mmol, 4.00 equiv) was added.
The resulting solution was stirred at ambient temperature for about 2 hours, and then saturated ammonium chloride was added.
Following standard extractive workup with ethyl acetate (3*50 mL), the crude residue was purified by silica gel column chromotagraphy (ethyl acetate/petroleum ether (1:2)) to give the title product as a light yellow oil (2.3 g; yield=38percent). LC-MS: m/z=122 (MH)+.
4.5 g
Stage #1: With isopropylmagnesium chloride In tetrahydrofuran at 0 - 20℃; for 6 h;
Stage #2: at 0 - 20℃;
To a solution of 5-bromo-2-methyl-pyridine (2.0 g, 11.6mmol) in anhydrous THF (20 mL) was added isopropylmagnesium chloride (2M in THF, 9.3 mL, 1.6 eq). dropwise over 30 mins at 0 °C under nitrogen atmosphere, then the reaction mixture was stirred at room temperature for 6 hrs. DMF (1.02 g, 1.2 eq) was added to the reation mixture at 0 °C for 30 mi amd the mixture was the stirred at room temperature for overnight. The reaction mixture was poured into water (50 mL), and the aqueous phase was extracted with EtOAc (50 mL x3). The extracts were washed with brine (50 mL), dried over Na2SO4 and concentrated in vacuum to give 4.5 g of crude 6-methylpyridine-3-carbaldehyde as yellow oil.

Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 12, p. 1877 - 1879
[2] Patent: WO2010/3048, 2010, A1, . Location in patent: Page/Page column 130-131
[3] Patent: WO2009/146358, 2009, A1, . Location in patent: Page/Page column 97
[4] Patent: US2010/125085, 2010, A1, . Location in patent: Page/Page column 16
[5] Patent: WO2016/123392, 2016, A2, . Location in patent: Paragraph 00595
  • 3
  • [ 5470-70-2 ]
  • [ 53014-84-9 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 25, p. 8415 - 8420
[2] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
[3] Patent: EP1184374, 2002, A1, . Location in patent: Page 29
[4] Patent: US2011/237584, 2011, A1,
[5] Patent: US2007/4772, 2007, A1,
[6] Patent: CN106349153, 2017, A, . Location in patent: Paragraph 0030; 0035; 0040; 0045; 0050; 0055; 0060
[7] Patent: WO2008/40934, 2008, A1,
[8] Patent: WO2009/110985, 2009, A2,
  • 4
  • [ 221615-71-0 ]
  • [ 53014-84-9 ]
Reference: [1] Patent: US2011/237584, 2011, A1, . Location in patent: Page/Page column 134
  • 5
  • [ 140-76-1 ]
  • [ 53014-84-9 ]
Reference: [1] Patent: US4559344, 1985, A,
  • 6
  • [ 21684-59-3 ]
  • [ 53014-84-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1989, vol. 32, # 3, p. 583 - 593
[2] Patent: EP3184527, 2017, A1,
[3] Patent: EP210782, 1991, B1,
  • 7
  • [ 221615-71-0 ]
  • [ 53014-84-9 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 25, p. 8415 - 8420
  • 8
  • [ 13061-96-6 ]
  • [ 149806-06-4 ]
  • [ 53014-84-9 ]
Reference: [1] Patent: WO2008/16968, 2008, A2, . Location in patent: Page/Page column 70
  • 9
  • [ 106837-80-3 ]
  • [ 53014-84-9 ]
Reference: [1] Gazzetta Chimica Italiana, 1956, vol. 86, p. 386,388
  • 10
  • [ 3222-48-8 ]
  • [ 53014-84-9 ]
Reference: [1] Gazzetta Chimica Italiana, 1956, vol. 86, p. 386,388
  • 11
  • [ 3222-47-7 ]
  • [ 53014-84-9 ]
Reference: [1] Patent: EP3184527, 2017, A1, . Location in patent: Paragraph 0625
  • 12
  • [ 53014-84-9 ]
  • [ 118420-23-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1989, vol. 32, # 3, p. 583 - 593
  • 13
  • [ 53014-84-9 ]
  • [ 221615-75-4 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 25, p. 8415 - 8420
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