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[ CAS No. 211122-38-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 211122-38-2
Chemical Structure| 211122-38-2
Chemical Structure| 211122-38-2
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Product Details of [ 211122-38-2 ]

CAS No. :211122-38-2 MDL No. :MFCD11616889
Formula : C8H8FNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ALCBYUWDBOVTGN-UHFFFAOYSA-N
M.W : 169.15 Pubchem ID :53419770
Synonyms :

Safety of [ 211122-38-2 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H311-H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 211122-38-2 ]

* 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.

  • Downstream synthetic route of [ 211122-38-2 ]

[ 211122-38-2 ] Synthesis Path-Downstream   1~20

  • 1
  • 2-fluoro-3-methylpyridine-5-carboxylic acid [ No CAS ]
  • [ 74-88-4 ]
  • [ 211122-38-2 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; 20.1 Step 1: Methyl 6-fluoro-5-methylnicotinate (103). A mixture of 5-methyl-6-fluoro-nicotinic acid 102 (7.0 g, 45 mmol), K2CO3 (13.7 g, 99 mmol) and methyl iodide (9.58 g, 67 mmol) in DMF (200 mL) was stirred for 16 h at room temperature. After dilution with water (50 mL), the reaction mixture was extracted with EtOAc (50 mL). The combined extracts were washed successively with sat. aqueous NaHCO3 solution (20 mL), sat. NaCl (2*20 mL) and dried (Na2SO4). Filtration and evaporation of the solvent gave the product 103 (6.5 g, 85%).
85% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; 8.1 Step 1: Methyl 6-fluoro-5-methylnicotinate (50). Step 1: Methyl 6-fluoro-5-methylnicotinate (50). A mixture of 5-methyl-6-fluoro- nicotinic acid 49 (7.0 g, 45 mmol), K2C03 (13.7 g, 99 mmol), methyl iodide (9.58 g, 67 mmol) and DMF (200 mL) was stirred for 16 h at RT. After dilution with water (50 mL), the reaction mixture was extracted with EtOAc (50 mL). The organic phase was washed successively with saturated aqueous NaHC03 (20 mL), brine (2 x 20 mL) and dried (Na2S04). Filtration and evaporation of the solvent gave 50 (6.5 g, 85%).
  • 2
  • [ 211122-38-2 ]
  • [ 75-31-0 ]
  • [ 1246391-50-3 ]
YieldReaction ConditionsOperation in experiment
98.4% at 90℃; for 12h; Sealed tube; 20.2 Step 2: Methyl 6-(isopropylamino)-5-methylnicotinate (104). In a sealed tube, a reaction mixture of isopropylamine (50 mL) and 103 (6.5 g, 38 mmol) was heated at 90° C. for 12 h. After it was cooled to room temperature, volatiles were removed in vacuo. The obtained residue was diluted with water and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated to afford 104 (7.9 g, 98.4%).
98.4% at 90℃; for 12h; Sealed tube; 8.2 Step 2: Methyl 6-(isopropylamino)-5-methylnicotinate (51). Step 2: Methyl 6-(isopropylamino)-5-methylnicotinate (51). Isopropylamine (50 mL) and 50 (6.5 g, 38 mmol) were combined in a sealed tube and heated at 90 °C for 12 h. After cooling to RT, volatiles were removed in vacuo. The resulting residue was diluted with water and extracted with EtOAc. The combined organic layers were dried over Na2S04 and concentrated to afford 51 (7.9 g, 98.4%).
  • 3
  • [ 753-90-2 ]
  • [ 211122-38-2 ]
  • 5-methyl-6-((2,2,2-trifluoroethyl)amino)nicotinic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% Stage #1: trifluoroethylamine; methyl 6-fluoro-5-methylnicotinate In 1-methyl-pyrrolidin-2-one at 220℃; for 2.5h; Microwave irradiation; Stage #2: With water; sodium hydroxide In methanol at 50℃; for 1h; Carboxylic acid-55: 5-methyl-6-((2,2,2-trifluoroethyl)amino)nicotinic acid A mixture of methyl 6-fluoro-5-methylnicotinate (2.00 g, 11.8 mmol) and 2,2,2-trifluoroethanamine (9.37 g, 95 mmol) in N-methylpyrrolidone (24 mL) is stirred at 220 oC for 2.5 hours under microwave irradiation. The mixture is diluted with MeOH (30 mL), and 2 M aqueous sodium hydroxide solution (15 mL) is added to the mixture. After stirring at 50 oC for 1 hour, the mixture is acidified by 2 M hydrochloric acid, and extracted with EtOAc/hexane (100 mLx3). The combined organic layer is washed with water (100 mL), and dried over sodium sulfate. After filtration, the filtrate is concentrated in vacuo. The residue is crystallized from diisopropyl ether to give 884 mg (32 %) of the title compound as a pale pink solid. 1H-NMR (300 MHz, DMSO-d6) delta 8.49 (1H, s), 7.78 (1H, s), 7.17 (1H, t, J = 6.6 Hz), 4.35-4.21 (2H, m), 2.14 (3H, s) (a signal due to COOH is not observed), MS (ESI) m/z: 233 (M-H) -.
  • 4
  • [ 2358-54-5 ]
  • [ 211122-38-2 ]
  • [ 1404115-78-1 ]
YieldReaction ConditionsOperation in experiment
74% Stage #1: 2,2,2-trifluoroethoxyethanol; methyl 6-fluoro-5-methylnicotinate With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 18 - 25℃; for 1h; Stage #2: With water; sodium hydroxide In methanol; N,N-dimethyl-formamide at 18 - 25℃; for 1h; Carboxylic acid-56: 5-methyl-6-(2-(2,2,2-trifluoroethoxy)ethoxy)nicotinic acid To a mixture of 2-(2,2,2-trifluoroethoxy)ethanol (1.64 g, 11.4 mmol) and potassium tert-butoxide (1.38 g, 12.3 mmol) in DMF (30 mL) is added 6-fluoro-5-methylnicotinate (1.60 g, 9.46 mmol) at 0 oC, and the mixture is stirred at rt for 1 hour. Then, MeOH (30 mL) and 0.7 M sodium hydroxide aqueous solution (45 mL) are added to the mixture. After stirring at rt for 1 hour, MeOH is evaporated in vacuo. The residual aqueous phase is acidified by 2 M hydrochloric acid, and the formed precipitate is collected by filtration to give 1.95 g (74%) of the title compound as a white solid. 1H-NMR (300 MHz, DMSO-d3) delta 12.98 (1H, br s), 8.55 (1H, s), 8.01 (1H, s), 4.52-4.49 (2H, m), 4.16 (2H, q, J = 9.5 Hz), 3.98-3.95 (2H, m), 2.19 (3H, s), MS (ESI) m/z: 280 (M+H) +.
  • 5
  • [ 211122-38-2 ]
  • 4,4-difluoropiperidine hydrochloride [ No CAS ]
  • 6-(4,4-difluoropiperidin-1-yl)-5-methylnicotinic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% Stage #1: methyl 6-fluoro-5-methylnicotinate; 4,4-difluoropiperidine hydrochloride With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 16h; Stage #2: With water; sodium hydroxide In methanol; N,N-dimethyl-formamide at 60℃; for 3h; Carboxylic acid-62: 6-(4,4-difluoropiperidin-1-yl)-5-methylnicotinic acid To a mixture of 2,2,2-trifluoroethanol (3.84 g, 38.4 mmol) and cesium carbonate (8.33 g, 25.6 mmol) in DMF (20 mL) is added ethyl 6-(chloromethyl)-5-methylnicotinate hydrochloride (1.37 g, 6.39 mmol, Step-3). After stirring at 40 oC for 20 hours, 2 M aqueous sodium hydroxide solution (20 mL), water (20 mL), THF (20 mL), and EtOH (20 mL) are added to the mixture. After stirring at 60 oC for 3 hours, the mixture is acidified by 2 M hydrochloric acid (pH is around 4). The organic solvent is removed by evaporation, and the residual aqueous layer is extracted with EtOAc/hexane. The separated organic layer is washed with water, dried over sodium sulfate, and concentrated in vacuo. The residue is crystallized from hexane to give 1.06 g (66%) of the title compound as a white solid. 1H-NMR (300 MHz, DMSO-d6) delta 8.85 (1H, d, J = 1.5 Hz), 8.11 (1H, s), 4.84 (2H, s), 4.22-4.12 (2H, m), 2.40 (3H, s) (a signal due to COOH is not observed), MS (ESI) m/z: 248 (M-H) -.
  • 6
  • [ 211122-38-2 ]
  • 5-methyl-6-((2,2,2-trifluoroethyl)amino)nicotinic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-methyl-pyrrolidin-2-one / 2.5 h / 22 °C / Microwave irradiation 2: water; sodium hydroxide / methanol / 1 h / 50 °C
  • 7
  • [ 211122-38-2 ]
  • 5-methyl-6-(3,3,3-trifluoropropoxy)nicotinic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.08 h / 0 °C 1.2: 2 h / 20 °C 2.1: water / tetrahydrofuran / 0.08 h / 0 °C
  • 8
  • [ 211122-38-2 ]
  • [ 1476027-21-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydride / mineral oil; tetrahydrofuran / 1 h / 0 °C 2: water; sodium hydroxide / tetrahydrofuran; ethanol / 1 h / 60 °C
  • 9
  • [ 371-41-5 ]
  • [ 211122-38-2 ]
  • [ 1476025-68-9 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 3h;
  • 10
  • [ 2516-33-8 ]
  • [ 211122-38-2 ]
  • C12H15NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h;
  • 11
  • [ 15878-00-9 ]
  • [ 211122-38-2 ]
  • [ 1476026-04-6 ]
  • 12
  • [ 753-90-2 ]
  • [ 211122-38-2 ]
  • C10H11F3N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1-methyl-pyrrolidin-2-one at 22℃; for 2.5h; Microwave irradiation;
  • 13
  • [ 2240-88-2 ]
  • [ 211122-38-2 ]
  • C11H12F3NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3,3,3-Trifluoropropanol With sodium hydride In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: methyl 6-fluoro-5-methylnicotinate In tetrahydrofuran at 20℃; for 2h;
  • 14
  • [ 211122-38-2 ]
  • [ 1246391-51-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 12 h / 90 °C / Sealed tube 2: hydrogenchloride / water / 12 h / 80 °C
  • 15
  • [ 67-56-1 ]
  • 2-fluoro-3-methylpyridine-5-carboxylic acid [ No CAS ]
  • [ 211122-38-2 ]
YieldReaction ConditionsOperation in experiment
With diazomethyl-trimethyl-silane In diethyl ether at 20℃; for 1h; 1-55: To a stirred soln of 2-fluoro-3-methyl-pyridine-5-carboxylic acid (3.50 g, 22.6 mmol) in MeOH (20 mL) was added 2M trimethylsilyldiazomethane in ethyl ether soln (22.0 mL, 44.0 mmol) at RT. After 1 h, acetic acid (8.0 mL) was added to quench the rxn. Solvent was removed under reduced pressure to provide compound 1-55.
  • 16
  • [ 211122-38-2 ]
  • [ 67-63-0 ]
  • C11H15NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride In N,N-dimethyl-formamide; mineral oil for 3h; 1-56: To a stirred soln of compound 1-55 (2.0 g, 12 mmol) in anhydrous DMF (8.0 mL) was added iPrOH (0.90 g, 15 mmol) and 60% NaH in mineral oil (0.60 g, 15 mmol). After 3 h, water (100 mL) was added to quench the rxn. The mixture was extracted with EtOAc (2x150 mL), washed with brine, dried over sodium sulfate and concentrated. The residue was purified via Combi-flash column on silica gel using a solvent gradient from 0- 20% EtOAc in heptanes to afford compound 1-56.
  • 17
  • [ 211122-38-2 ]
  • [ 1011558-18-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 3 h 2: water; sodium hydroxide / methanol / 2 h / Reflux
  • 18
  • [ 211122-38-2 ]
  • C22H18Cl2N2O3 [ No CAS ]
  • C29H23Cl2N3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In N,N-dimethyl-formamide at 110℃; for 12h; 43 Example 43: Compound 43 To a solution of 31-2 (200 mg, 465.88 µmol) and 43-1 (120 mg, 709.42 µmol) in N,N-dimethylformamide (5 ml), cesium carbonate (455 mg, 1.40 mmol) was added. The reaction mixture was stirred at 110 °C for 12 hours. After the reaction was completed, the mixture was added with water (20 ml), adjusted with 1 M of hydrochloric acid to pH=6, and extracted with ethyl acetate (30 ml) for 3 times. The combined organic phase was washed with saturated brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated to obtain a crude product. The crude product was separated by preparative chromatography to give the target compound 43. 1H NMR (400MHz, METHANOL-d4) δ = 8.98 (s, 1H), 8.44 (s, 1H), 7.52 - 7.48 (m, 2H), 7.47-7.41 (m, 1H), 6.75 (d, J=2.0 Hz, 1H), 6.52 (dd, J=2.8, 8.8 Hz, 1H), 5.98 (d, J=8.5 Hz, 1H), 4.84-4.84 (m, 2H), 3.12 - 2.98 (m, 2H), 2.82 - 2.73 (m, 2H), 2.30 (td, J=6.8, 13.6 Hz, 1H), 2.18 (s, 3H), 1.22 - 1.14 (m, 4H). MS m/z: 564.0 [M+H]+.
  • 19
  • [ 211122-38-2 ]
  • 4-(tert-butyl)-1H-pyrazole [ No CAS ]
  • 6-(4-tert-butylpyrazol-1-yl)-5-methylpyridine-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 100 °C 2: methanol; sodium hydroxide / tetrahydrofuran / 1 h / 25 °C
  • 20
  • [ 211122-38-2 ]
  • 4-(tert-butyl)-1H-pyrazole [ No CAS ]
  • 6-(4-tert-butylpyrazol-1-yl)-5-methylpyridine-3-carboxylic acid [ No CAS ]
  • methyl 6-(4-tert-butylpyrazol-1-yl)-5-methylpyridine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 68.7% 2: 25.4% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 1h; A.62.a Step a) Methyl 6-(4-tert-butylpyrazol-1-yl)-5-methyl-pyridine-3-carboxylate Methyl 6-fluoro-5-methylnicotinate (370 mg, 2.98 mmol) and K2C03 (1.03 g, 7.42 mmol)were combined and stirred in DMF (2 mL) for 10 minutes, then 4-tert-butylpyrazole (500mg, 2.96 mmol) was added and the reaction was stirred for 1 h at 100 °C. The reaction mixture was adjusted to pH 3-4 with HC1 (1 M), extracted with MTBE. The combined organic layer was washed with HC1 (1M) and brine, dried over Na2504, filtered and concentrated providing the title compound (555 mg, 2.03 mmol, 68.7%) and hydrolysed side product (6-(4-tert-butylpyrazol- l-yl)-5 -methyl-pyridine-3 -carboxylic acid, A. 62) (195.0 mg, 752.0 imol, 25.4%) as white solid.MS (ESI): m/z = 274.3 [M+Hj for title compoundMS (ESI): m/z = 260.2 [M+Hj for hydrolysed side product A.62
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