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[ CAS No. 1251844-44-6 ] {[proInfo.proName]}

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Product Details of [ 1251844-44-6 ]

CAS No. :1251844-44-6 MDL No. :MFCD22690248
Formula : C8H7F2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :FDVNQZVPNUJODO-UHFFFAOYSA-N
M.W : 187.14 Pubchem ID :59536559
Synonyms :

Safety of [ 1251844-44-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1251844-44-6 ]

* 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 [ 1251844-44-6 ]

[ 1251844-44-6 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 1251844-44-6 ]
  • [ 1251844-45-7 ]
YieldReaction ConditionsOperation in experiment
75% With hydrogen; acetic acid at 20℃; for 13h; 39.3 Methyl 2-(difluoromethyl)isonicotinate (2.4 g, 12.82 mmol) was dissolved in acetic acid (40 mL). Platinum(IV) oxide (0.291 g, 1.28 mmol) was added and the mixture was hydrogenated at 5 bar and room temperature for 7 h in a Büchi hydrogenation apparatus. The catalyst was removed by filtration, fresh platinum(IV) oxide (210 mg, 0.92 mmol) was added and the hydrogenation was continued at 5 bar and room temperature for 6 h. The catalyst was removed by filtration and the solvent evaporated. The residue was taken up in DCM and the organic phase was washed with satd NaHCO3. The aqueous phase was extracted with DCM and the combined organic phases were filtered through a phase separator and evaporated. Methyl 2-(difluoromethyl)piperidine-4-carboxylate (1.85 g, 75%) was isolated. MS m/z 194 (M+H)+
  • 2
  • [ 125104-34-9 ]
  • [ 1251844-44-6 ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: methyl 2-formylpyridine-4-carboxylate With diethylamino-sulfur trifluoride In dichloromethane at 0 - 20℃; for 2h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water at 0℃; 39.2 Methyl 2-formylisonicotinate (2.51 g, 15.20 mmol) was dissolved in dichloromethane (50 mL) and cooled to 0° C. Diethylaminosulfur trifluoride (DAST) (2.61 mL, 19.76 mmol) was added dropwise. The cooling was removed and the mixture was stirred at room temperature for 2 h. Satd NaHCO3 was added at 0° C. and the phases were separated. The aqueous phase was extracted with DCM. The combined organic phases were filtered through a phase separator and evaporated. The residue was purified by automated flash chromatography on a Biotage KP-SIL 50 g column. 5:1 of EtOAc in heptane over 10 CV was used as mobile phase. Methyl 2-(difluoromethyl)isonicotinate (2.4 g, 84%) was isolated. 1H NMR (400 MHz, cdcl3) δ 4.00 (s, 3H), 6.70 (t, 1H), 7.97 (d, 1H), 8.19 (s, 1H), 8.82 (d, 1H).
  • 3
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 1211580-54-9 ]
  • [ 1251844-44-6 ]
YieldReaction ConditionsOperation in experiment
500 mg With triethylamine; diphenyl(pyren-1-yl)phosphane; In N,N-dimethyl-formamide; at 120℃; under 12160.8 Torr; for 8h;Sealed tube; Description 129Methyl 2-(difluoromethyl)isonicotinate (D129)F11:10To a mixture of <strong>[1211580-54-9]4-bromo-2-(difluoromethyl)pyridine</strong> (D128, 900 mg), DPPP (357 mg),triethylamine (0.603 mL) in methanol (20 mL) and DMF (5 mL) was passed CO gas for 3 mm. The mixture was then heated to 120C in a sealed vial at 16 atm for 8 hours. After cooling to RT, the mixture was concentrated. Water was added, extracted with EtOAc (3 x50 mL). The organic layer was washed with saturated NaHCO3 solution (10 mL), water (10 mL), and brine (10 mL), dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography (silicagel, petroleum ether/EtOAc = 5:1) to afford the title compound (500 mg) as yellow oil. MS (ESI):C8H7F2N02 requires 187; found 188 [M+H].
  • 4
  • [ 1251844-44-6 ]
  • [ 1256818-14-0 ]
YieldReaction ConditionsOperation in experiment
400 mg With water; sodium hydroxide In methanol at 20℃; 130 Description 1302-(Difluoromethyl)isonicotinic acid (D130) Description 1302-(Difluoromethyl)isonicotinic acid (D130)NF(iy0HF 0A mixture of methyl 2-(difluoromethyl)isonicotinate (D129, 500 mg), NaOH (1069 mg) in water (10 mL) and MeOH (10 mL) was stirred at RT overnight. The mixture was concentrated and adjusted to pH < 7 with 2 M HC1, then extracted with EtOAc (3 x50 mL). The organic layer was washed with saturated NaHCO3 solution (10 mL), water (10 mL), and brine (10 mL), dried over MgSO4, filtered and concentrated to afford the title compound (400 mg) as white solid. MS (ESI):C7H5F2N02 requires 173; found 174 [M+H].
  • 5
  • [ 1251844-44-6 ]
  • [ 1225047-28-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: water; sodium hydroxide / methanol / 20 °C 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C
  • 6
  • [ 131747-63-2 ]
  • [ 1251844-44-6 ]
  • 7
  • [ 2459-09-8 ]
  • [ 275818-95-6 ]
  • [ 1251844-44-6 ]
YieldReaction ConditionsOperation in experiment
50% With dipotassium peroxodisulfate; In dimethyl sulfoxide; at 90℃; for 12h; General procedure: To a 10 mL Schlenk tube, coumarin 1a (0.3 mmol, 1 equiv),difluoromethane-sulfinate (0.6 mmol, 2 equiv), K2S2O8 (3 equiv.)were dissolved in DMSO (2.0 mL). Then the mixture was stirred at90 C for 12 h. To the residue was added water (10 mL) andextracted with ethyl acetate (5 mL 3). The combined organicfractions were dried over Na2SO4, and concentrated under vacuumto yield the crude product, which was purified by column chromatographyto give the target product. The same procedure was applied for to produce other compounds, after purification by silicagel column chromatography (EA: PE 1/10 to 1/2).
100%Chromat. With tert.-butylhydroperoxide; trifluoroacetic acid; In dichloromethane; water; at 20℃; for 1h;pH 7.0; General procedure: A mixture of 104 mg (0.77 mmol) of methyl pyridine-4-carboxylate, 522 mg (3.78 mmol) of <strong>[275818-95-6]sodium difluoromethanesulfinate</strong>, and 1.3 mL of water was stirred on a magnetic stirrer, trifluoroacetic acid was added to pH 7, and an additional 120 mg (1.08 mmol) of trifluoroacetic acid was then added. Methylene chloride, 3 mL, was added, and 360 mg (4 mmol) of tert-butyl hydroperoxide was added in 20-25-mg portions over a period of 15 min. The flask was capped with a septum, and the mixture was stirred for 1 h at room temperature on a magnetic stirrer. The mixture was treated with 6 mL of a saturated aqueous solution of NaHCO3, 6 mL of methylene chloride was added, and the mixture was stirred for 10 min on a magnetic stirrer. The organic phase was separated, the aqueous phase was extracted with methylene chloride (3 x 6 mL), the extracts were combined with the organic phase and dried over Na2SO4, and the solvent was distilled off. Yield of crude product mixture 74 mg (60%). Compound 7a was isolated by column chromatography using methylene chloride as eluent; yield 39%, Rf 0.56. Compounds 7b-7d were identified by GC/MS. Methyl 2-(difluoromethyl)pyridine-4-carboxylate(7a). Oily material. 1H NMR spectrum (CDCl3), δ, ppm: 4.00 s (3H, OMe), 6.71 t (1H, JHF = 55.0 Hz), 7.96 d (1H, J = 5.0 Hz), 8.20 s (1H), 8.82 d (1H, J = 5.0 Hz). 13C NMR spectrum (CDCl3), δC, ppm: 52.96 (Me), 113.46 t (CHF2, JCF = 241.0 Hz), 119.60, 124.66, 138.87, 150.39, 153.94 t (JCF = 26.4 Hz), 164.72 (C=O). 19F NMR spectrum (CDCl3): δF -116.12 ppm. Mass spectrum (EI), m/z (Irel, %): 188 (6), 187 (61) [M]+, 186 (4), 168 (6), 157 (8), 156 (100) [M - H3O]+, 136 (14), 129 (6), 128 (78) [M - CH3COO]+, 108 (9), 101 (12), 82 (5), 81 (4), 78 (15), 77 (5), 76 (4), 51 (43), 50 (16). Mass spectrum (ESI): m/z 188.0513 [M + H]+. C8H8F2NO2. Calculated: [M + H]+ 188.0518.
  • 8
  • [ 2459-09-8 ]
  • [ 275818-95-6 ]
  • [ 1251844-44-6 ]
  • methyl 3-(difluoromethyl)pyridine-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
39%; 10%Chromat. With tert.-butylhydroperoxide; trifluoroacetic acid; In dichloromethane; water; at 20℃; for 1h;pH 7.0; A mixture of 104 mg (0.77 mmol) of methyl pyridine-4-carboxylate, 522 mg (3.78 mmol) of <strong>[275818-95-6]sodium difluoromethanesulfinate</strong>, and 1.3 mL of water was stirred on a magnetic stirrer, trifluoroacetic acid was added to pH 7, and an additional 120 mg (1.08 mmol) of trifluoroacetic acid was then added. Methylene chloride, 3 mL, was added, and 360 mg (4 mmol) of tert-butyl hydroperoxide was added in 20-25-mg portions over a period of 15 min. The flask was capped with a septum, and the mixture was stirred for 1 h at room temperature on a magnetic stirrer. The mixture was treated with 6 mL of a saturated aqueous solution of NaHCO3, 6 mL of methylene chloride was added, and the mixture was stirred for 10 min on a magnetic stirrer. The organic phase was separated, the aqueous phase was extracted with methylene chloride (3 x 6 mL), the extracts were combined with the organic phase and dried over Na2SO4, and the solvent was distilled off. Yield of crude product mixture 74 mg (60%). Compound 7a was isolated by column chromatography using methylene chloride as eluent; yield 39%, Rf 0.56. Compounds 7b-7d were identified by GC/MS. Methyl 2-(difluoromethyl)pyridine-4-carboxylate(7a). Oily material. 1H NMR spectrum (CDCl3), δ, ppm: 4.00 s (3H, OMe), 6.71 t (1H, JHF = 55.0 Hz), 7.96 d (1H, J = 5.0 Hz), 8.20 s (1H), 8.82 d (1H, J = 5.0 Hz). 13C NMR spectrum (CDCl3), δC, ppm: 52.96 (Me), 113.46 t (CHF2, JCF = 241.0 Hz), 119.60, 124.66, 138.87, 150.39, 153.94 t (JCF = 26.4 Hz), 164.72 (C=O). 19F NMR spectrum (CDCl3): δF -116.12 ppm. Mass spectrum (EI), m/z (Irel, %): 188 (6), 187 (61) [M]+, 186 (4), 168 (6), 157 (8), 156 (100) [M - H3O]+, 136 (14), 129 (6), 128 (78) [M - CH3COO]+, 108 (9), 101 (12), 82 (5), 81 (4), 78 (15), 77 (5), 76 (4), 51 (43), 50 (16). Mass spectrum (ESI): m/z 188.0513 [M + H]+. C8H8F2NO2. Calculated: [M + H]+ 188.0518. Methyl 3-(difluoromethyl)pyridine-4-carboxylate (7b). Mass spectrum, m/z (Irel, %): 188 (7), 187 (80) [M]+, 156 (100) [M - CH3O]+, 155 (21), 152 (47), 128 (87) [M -CH3COO]+, 127 (13), 124 (13), 108 (16), 96 (13), 75 (19), 51 (38), 50 (14).
  • 9
  • [ 58481-11-1 ]
  • [1,3-bis[2,6-bis(1-methylethyl)phenyl]-2-imidazolidinylidene](difluoromethyl)silver [ No CAS ]
  • [ 1251844-44-6 ]
YieldReaction ConditionsOperation in experiment
62% With bis[2-(diphenylphosphino)phenyl] ether; bis(dibenzylideneacetone)-palladium(0) In toluene at 80℃; for 18h; Inert atmosphere;
  • 10
  • [ 381-73-7 ]
  • [ 2459-09-8 ]
  • [ 1251844-44-6 ]
YieldReaction ConditionsOperation in experiment
70% With potassium peroxodisulfate; silver(I) nitrate; trifluoroacetic acid In lithium hydroxide monohydrate; acetonitrile at 50℃; for 24h;
71 %Spectr. With potassium peroxodisulfate; silver(I) nitrate In lithium hydroxide monohydrate; acetonitrile at 50℃; Sealed tube; regioselective reaction;
  • 11
  • [ 381-73-7 ]
  • [ 2459-09-8 ]
  • [ 1251844-44-6 ]
  • methyl 3-(difluoromethyl)isonicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 60% 2: 6% With potassium peroxodisulfate; silver(I) nitrate In lithium hydroxide monohydrate; acetonitrile at 50℃; for 24h; regioselective reaction;
27% With potassium peroxodisulfate; silver(I) nitrate In lithium hydroxide monohydrate; acetonitrile at 50℃; for 24h;
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