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[ CAS No. 153122-60-2 ]

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Chemical Structure| 153122-60-2
Chemical Structure| 153122-60-2
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Product Details of [ 153122-60-2 ]

CAS No. :153122-60-2 MDL No. :MFCD12912365
Formula : C7H7BClFO3 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :204.39 g/mol Pubchem ID :10932600
Synonyms :

Safety of [ 153122-60-2 ]

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

Application In Synthesis of [ 153122-60-2 ]

  • Downstream synthetic route of [ 153122-60-2 ]

[ 153122-60-2 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 153122-60-2 ]
  • 2-Bromoimidazo[1,2-a]pyridine [ No CAS ]
  • [ 153122-61-3 ]
YieldReaction ConditionsOperation in experiment
bis(triphenylphosphine)palladium(II)-chloride; In water; ethyl acetate; Step C A mixture of 0.8 g (4.1 mmol) of 2-bromoimidazo[1,2-a]pyridine, 0.8 g (4.2 mmol) of <strong>[153122-60-2]4-chloro-2-fluoro-5-methoxyphenylboronic acid</strong>, and 0.2 g (0.28 mmol) of bis(triphenylphosphine)palladium(II) chloride were heated in 30 ml of glyme at reflux for 2 h. The reaction mixture was partitioned between 250 ml of ethyl acetate and 100 ml of water and the separated organic layer washed with brine and dried over magnesium sulfate. On evaporating in vacuo, the remaining residue was flash chromatographed on silice gel (1:1 hexane/ethyl acetate) to afford 0.7 g of the title compound (m.p. 139-141 C.). NMR (CDCl3, 400 MHz): delta4.03 (s, 3H), 6.81 (t, 1H), 7.21 (m, 2H), 8.63 (d, 1H), 7.92 (d, 1H), 8.04 (s, 1H), 8.14 (d, 1H).
  • 2
  • 2,3-dichloro-5-methylsulfinylpyridine [ No CAS ]
  • [ 153122-60-2 ]
  • [ 203736-52-1 ]
YieldReaction ConditionsOperation in experiment
2.2 g (30%) With sodium bicarbonate;tetrakis(triphenylphosphine)palladium (0); In tetrahydrofuran; water; Example 6 3-Chloro-2-(4-chloro-2-fluoro-5-methoxyphenyl)-5-methylsulfinylpyridine 4.6 g of 2,3-dichloro-5-methylsulfinylpyridine, 4.5 g of <strong>[153122-60-2]4-chloro-2-fluoro-5-methoxybenzeneboronic acid</strong>, 5.5 g of sodium hydrogen carbonate and 1.0 g of tetrakis(triphenylphosphine)palladium(0) were refluxed for 180 hours in a mixture of 100 ml of water and 100 ml of tetrahdyrofuran. After the tetrahydrofuran has been evaporated, the residue was extracted four times with in each case 70 ml of MTB. The combined organic phases were then dried over sodium sulfate and finally concentrated. The resulting oil was purified by means of chromatography on silica gel (eluent: cyclohexane/MTB=7:3?1:1 and cyclohexane/ethyl acetate=2:1). Stirring this purified oil with diethyl ether gave 2.2 g (30%) of white crystals.; m.p.: 117-118 C.
  • 3
  • aqueous hydrogen chloride [ No CAS ]
  • [ 153122-59-9 ]
  • [ 121-43-7 ]
  • [ 153122-60-2 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; In diethyl ether; hexane; Step B To 2.0 g (7.0 mmol) of 2-chloro-4-fluoro-5-iodo-anisole (made from the compound of Example 11, Step A by methylation) stirring in 30 ml of diethyl ether at -78 C., 4.8 ml (7.7 mmol) of 1.6M n-butyl lithium was added dropwise (keeping the temperature below -69 C.). After stirring 0.5 h, 0.91 ml (8.0 mmol) of trimethyl borate in 15 ml of diethyl ether was added dropwise and the reaction mixture stirred 3 h before allowing to warm to room temperature. Slowly, 1N aqueous hydrogen chloride was added and the resulting biphase system stirred 1 h. The separated aqueous phase was separated and washed with an additional 30 ml of diethyl ether. Combined organic layers were washed with brine and dried over magnesium sulfate. Evaporating in vacuo gave a white solid which was suspended in hexane, filtered, and dried to afford 0.86 g of a technical sample of 4-chloro-2-fluoro-5-methoxyphenylboronic acid (m.p. 280-290 C.).
  • 4
  • [ 153122-59-9 ]
  • [ 121-43-7 ]
  • [ 153122-60-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; n-butyllithium; In hexane; nitrogen; Petroleum ether; (2) 90ml of ether solution containing 6.01g (21mmol) of the compound obtained in the Reference Example 8(1) were stirred in the stream of nitrogen gas at -78ØC, followed by dropwise addition of n-butyl lithium (1.5M in hexane, 15.0ml, 23mmol) for 15 minutes and stirring at the above temperature for 30 minutes. Then, 40ml of ether solution containing 2.6g (25mmol) of trimethyl borate were dropwise added at temperature between -70ØC and -78ØC for 1 hour and the mixture was stirred at the same temperature for 3 hours. The mixture was left to stand at room temperature overnight, whereby the temperature was raised to the room temperature. 60ml of 1N hydrochloric acid was dropwise added under water cooling with water and the mixture was stirred at room temperature for 1 hour. The ether layer was separated, and the aqueous layer was extracted with ether. The ether layers were combined, washed with brine, dried and concentrated by evaporation of solvent. A small amount of petroleum ether was added to the residue, and the deposited crystals were collected by filtration and dried to obtain 2.69g of 4-chloro-2-fluoro-5-methoxyphenylboronic acid. m.p.289-291ØC 1H-NMR(DMSO-d6) delta 3.84(3H, s), 7.22-7.28(2H, m), 8.15-8.40(2H, br) 19F-NMR(DMSO-d6) 6 -112.6 IR(Nujol) 3522, 3350, 1603, 1053, 944, 878, 785 cm-1
  • 5
  • [ 17180-93-7 ]
  • [ 110-71-4 ]
  • dichlorobis(triphenylphosphine)paradium [ No CAS ]
  • 4-chloro-5-cyano-6-difluoromethylpyrimidine [ No CAS ]
  • [ 153122-60-2 ]
  • dichlorobis(triphenylphosphine)palladium[II] [ No CAS ]
  • [ 425406-70-8 ]
YieldReaction ConditionsOperation in experiment
With sodium bicarbonate; In water; Example 49 4-(4-Chloro-2-fluoro-5-methoxyphenyl)-5-cyano-6-difl uoro- methylpyrimidine (Compound No. K-22) 4-Chloropyrimidine 0.15 g (0.79 mmol) prepared in the Reference Example 17, 4-chloro-2-fluoro-5-methoxyphenyl-boronic acid 0.18 g (0.88 mmol), dichlorobis(triphenyl-phosphine)palladium(II) 0.08 g (0.11 mmol) and sodium hydrogen carbonate 0.135 g (1.61 mmol) were added to a mixture of 1,2-dimethoxyethane 7 ml and water (three drops). The mixture was stirred at 55ØC for 16 hours, and then cooled. The reaction mixture was adjusted to pH 3 with dilute hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried and evaporated to remove the solvent. The residue was purified by silica gel column chromatography in a solvent system of hexane and ethyl acetate (4: 1) to give 4-(4-chloro-2-fluoro-5-methoxyphenyl)-5-cyano-6-difluoro-methylpyrimidine (0.025 g). m.p. 113-115ØC 1H-NMR(CDCl3) delta 3.97 (3H, s), 6.81 (1H, t, J=53.2Hz), 7.18 (1H, d, J=6.1Hz), 7.38 (1H, d, J=9.3Hz), 9.51 (1H, s) IR(nujol): 2200 cm-1
  • 6
  • dichlorobis(triphenylphosphine)paradium [ No CAS ]
  • [ 153122-60-2 ]
  • [ 83942-10-3 ]
  • 5-chloro-4-(4-chloro-2-fluoro-5-methoxyphenyl)-6-methylpyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In 1,2-dimethoxyethane; chloroform; water; (1) To a mixture of dimethoxyethane (25ml) and water(5m1) were added <strong>[83942-10-3]4,5-dichloro-6-methylpyrimidine</strong> (0.5g, 3.06mmol), 4-chloro-2-fluoro-5-methoxyphenylboronic acid (0.63g, 3.06mmol), dichlorobis(triphenylphosphine)paradium (II) (0.21g, 0.3mmol) and sodium hydrogencarbonate (0.84g, 10mmol). The mixture was heated under reflux for 2 hours. After cooling, the reaction mixture was neutralized to pH 2 with 2N-hydrochloric acid, and evaporated to remove the dimethoxyethane. The residue was dissolved in chloroform, and the solution was washed with water, dried, then evaporated to remove the solvent. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2) to give 5-chloro-4-(4-chloro-2-fluoro-5-methoxyphenyl)-6-methylpyrimidine (0.6g). m.p.136-140ØC 1H-NMR(CDCl3) delta 2.72(3H, s), 3.92(3H, s), 6.99(1H, d, J=6.04Hz), 7.26(1H, d, J=8.92Hz), 9.01(1H, s)
  • 7
  • [ 141602-36-0 ]
  • [ 153122-60-2 ]
  • dichlorobis(triphenylphosphine)palladium[II] [ No CAS ]
  • 5-chloro-4-(4-chloro-2-fluoro-5-methoxyphenyl)-6-trifluoromethylpyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; (1) 4,5-Dichloro-6-trifluoromethylpyrimidine (1.3g, 6mmol), <strong>[153122-60-2]4-chloro-2-fluoro-5-methoxyphenylboronic acid</strong> (1.29g, 6.3mmol), dichlorobis (triphenylphosphine) palladium(II) (0.29g, 6.3mmol) and sodium hydrogencarbonate (1.64g, 20mmol) were added to a mixture of dimethoxyethane (50ml) and water (10ml). The resulting mixture was refluxed for 2 hours. After cooling, the reaction mixture was adjusted to pH 4 with 1N-hydrochloric acid and then concentrated. Water (60ml) was added to the residue, and the mixture was extracted with chloroform, washed with water, dried, and then concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 5-chloro-4-(4-chloro-2-fluoro-5-methoxyphenyl)-6-trifluoromethylpyrimidine (1.42g, compound no. A-1). m.p.:109-111ØC 1H-NMR(CDCl3) delta 3.94(3H, s), 7.01(1H, d, J=6.0Hz), 7.31(1H, d, J=9.0Hz), 9.28(1H, s). 19F-NMR(CDCl3) delta -68.1, -120.2.
  • 8
  • [ 110-71-4 ]
  • [ 153122-60-2 ]
  • [ 425407-32-5 ]
  • 4-(4-chloro-2-fluoro-5-methoxyphenyl)-5-formyl-6-methoxypyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium bicarbonate;dichlorobis(triphenylphosphine)palladium[II]; In water; ethyl acetate; (2) The compound 0.2 g (1.16 mmol) prepared in Example 46(1), sodium hydrogen carbonate 0.3 g (3.6 mmol), and dichlorobis(triphenylphosphine)palladium(II) 0.03 g (0.04 mmol) were added to a mixture of 1,2-dimethoxyethane (10 ml) and water (2 ml). The mixture was heated to 70ØC, and <strong>[153122-60-2]4-chloro-2-fluoro-5-methoxyphenylboronic acid</strong> 0.26 g (1.27 mmol) was portionwise added. The mixture was stirred at the same temperature for 2 hours, cooled, and, after addition of water, extracted with ethyl acetate. The extract was dried and evaporated to remove the solvent. The residue was purified by silica gel column chromatography in a solvent system of hexane and ethyl acetate (2:1) to give 4-(4-chloro-2-fluoro-5-methoxyphenyl)-5-formyl-6-methoxypyrimidine (0.21 g). m.p. 161-163ØC 1H-NMR(CDCl3) delta 3.94 (3H, s), 4.18 (3H, s), 7.12 (1H, d, J=6.1Hz), 7.20 (1H, d, J=9.2Hz), 8.94 (1H, s), 10.30 (1H, s) IR(Nujol):1696 cm-1
  • 9
  • [ 153122-60-2 ]
  • [ 39620-04-7 ]
  • [ 431942-76-6 ]
YieldReaction ConditionsOperation in experiment
17.5 2-(2-Fluoro-4-chloro-5-methoxyphenyl-1-yl)-3-chloro-4-amino-5-trifluoromethylpyridine Analogously to the procedure described in Example 1.5, 2.0 g (8.7 mmol) of the aminochloropyridine of Example 17.4 were treated with 2-fluoro-4-chloro-5-methoxyphenylboronic acid. Chromatography of the crude product on silica gel with cyclohexane/ethyl acetate (15/1, v/v) gave 1.0 g of the title compound. 1H NMR (d6-DMSO): delta (ppm)=8.4 (s, 1H), 7.6 (d, 2H), 7.2 (d, 2H), 3.9 (s, 3H). The NH2 signal is located broadly under the H2O signal.
  • 10
  • [ 2402-77-9 ]
  • [ 153122-60-2 ]
  • [ 431942-45-9 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate;tetrakis(triphenylphosphine)palladium (0); In tetrahydrofuran; tert-butyl methyl ether; water; 1.5 2-(2-Fluoro-4-chloro-5-methoxyphenyl-1-yl)-3-chloro-4-methyl-5-trifluoromethylpyridine 4.5 g (0.019 mol) of the dichloropyridine of Example 1.4, 4.0 g (0.019 mol) of <strong>[153122-60-2]2-fluoro-4-chloro-5-methoxyphenylboronic acid</strong>, 1.1 g (0.001 mol) of tetrakistriphenylphosphine palladium and 12.0 g of sodium hydrogencarbonate in 150 ml of THF and 150 ml of water were refluxed for 20 hours with stirring. After cooling, the phases were separated, the aqueous phase was extracted twice using in each case 100 ml of methyl tert-butyl ether, and the combined organic phases were dried over sodium sulfate and concentrated in vacuo. Chromatography of the residue on silica gel with cyclohexane/ethyl acetate (100:1, v/v) yielded 2.4 g of 2-(2-fluoro-4-chloro-5-methoxyphenyl-1-yl)-3-chloro-4-methyl-5-trifluoromethylpyridine. 1H NMR (CDCl3): delta (ppm)=8.8 (s, 1H), 7.3 (d, 1H), 7.0 (d, 1H), 3.9 (s, 3H), 2.6 (s, 3H).
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