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[ CAS No. 850568-47-7 ]

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Chemical Structure| 850568-47-7
Chemical Structure| 850568-47-7
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Product Details of [ 850568-47-7 ]

CAS No. :850568-47-7 MDL No. :MFCD06659820
Formula : C7H8BClN2O2 Boiling Point : 454°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :198.41 g/mol Pubchem ID :44118766
Synonyms :

Safety of [ 850568-47-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 850568-47-7 ]

  • Downstream synthetic route of [ 850568-47-7 ]

[ 850568-47-7 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 850568-47-7 ]
  • [ 13959-01-8 ]
  • 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-8-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; at 120.0℃; for 18h; Sodium acetate (410 mg, 5 mmol) and 1,1'- bis(diphenylphosphino)ferrocene palladium (II) chloride (complexed with dichloromethane) (36 mg, 0.05 mmol) were added to a mixture of ethyl 3-bromo-4- pyridine carboxylate (230 mg, 1.0 mmol) and <strong>[850568-47-7]2-amino-4-cyanophenylboronic acid hydrochloric acid salt</strong> (179 mg, 0.9 mmol). The mixture was connected to an exit bubbler and heated to 12O0C for 18 hours at which time LCMS analysis indicated that the reaction was done based on the disappearance of starting material. After cooling to room temperature, water was added and the dark solids were filtered and washed with dichloromethane to give 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-8- carbonitrile (156 mg) as a gray solid which was sufficiently pure enough for subsequent chemical transformations. LCMS (ESI) 222.4 (M+l)+. 1HNMR (400 MHz, DMSOd6) 12.2 (IH, s), 9.96 (IH, s), 8.90 (IH, d, 5.1 Hz), 8.77 (IH, d, 8.2 Hz), 8.13 (IH, d, 5.1 Hz), 7.73 (IH, dd 8.2, 1.6 Hz), 7.70 (IH, d, 1.6 Hz).
With sodium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dichloromethane; at 120.0℃; for 18h; Sodium acetate (410 mg, 5 mmol) and 1,1'-bis(diphenylphosphino)ferrocene palladium (II) chloride (complexed with dichloromethane) (36 mg, 0.05 mmol) were added to a mixture of ethyl 3-bromo-4-pyridine carboxylate (230 mg, 1.0 mmol) and <strong>[850568-47-7]2-amino-4-cyanophenylboronic acid hydrochloric acid salt</strong> (179 mg, 0.9 mmol). The mixture was connected to an exit bubbler and heated to 120 C. for 18 hours at which time LCMS analysis indicated that the reaction was done based on the disappearance of starting material. After cooling to room temperature, water was added and the dark solids were filtered and washed with dichloromethane to give 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-8-carbonitrile (156 mg) as a gray solid which was sufficiently pure enough for subsequent chemical transformations. LCMS (ESI) 222.4 (M+1)+. 1HNMR (400 MHz, DMSO-d6) 12.2 (1H, s), 9.96 (1H, s), 8.90 (1H, d, 5.1 Hz), 8.77 (1H, d, 8.2 Hz), 8.13 (1H, d, 5.1 Hz), 7.73 (1H, dd 8.2, 1.6 Hz), 7.70 (1H, d, 1.6 Hz).
  • 2
  • [ 755027-18-0 ]
  • [ 850568-47-7 ]
  • [ 1025369-59-8 ]
YieldReaction ConditionsOperation in experiment
With cesium fluoride;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 100℃; for 36h; To a mixture of the product from Step 1, -bromo-4-iodo-2-methoxybenzene (750 mg, 2.4 mmol), CsF (1.09 g, 7.2 mmol), <strong>[850568-47-7](2-amino-4-cyanophenyl)boronic acid hydrochloride</strong> (390 mg, 2.4 mmol), and Pd(PPh3)4 (277 mg, 0.24 mmol) was added DME (15 mL) under nitrogen. It was then heated to 100C. After 36 hours, EtOAc and water were added to the resulting thick red suspension. The organic layer was washed with brine, dried over Na2SO4, and the solvent was removed in vacuo. The residue was purified on silica (gradient EPO <DP n="52"/>elution, 3-50% EtO Ac/hex anes) to yield the title compound as a red oil. LRMS (M+H)+ =303.1.
With cesium fluoride;Pd(PPh3)4; In 1,2-dimethoxyethane; water; ethyl acetate; Step 2: 2-amino-4'-bromo-3'-methoxybiphenyl-4-carbonitrile To a mixture of the product from Step 1, -bromo-4-iodo-2-methoxybenzene (750 mg, 2.4 mmol), CsF (1.09 g, 7.2 mmol), <strong>[850568-47-7](2-amino-4-cyanophenyl)boronic acid hydrochloride</strong> (390 mg, 2.4 mmol), and Pd(PPh3)4 (277 mg, 0.24 mmol) was added DME (15 mL) under N2. It was then heated to 100 C. After 36 h, to the thick red suspension was added EtOAc and water. The organic layer was washed with brine, dried over Na2SO4, and the solvent was removed in vacuo. The residue was purified on silica (gradient elution, 3-50% EtOAc/hex) to yield the title compound as a red oil. LRMS (M+H)+=303.1.
  • 3
  • [ 26137-08-6 ]
  • [ 850568-47-7 ]
  • [ 1186040-15-2 ]
YieldReaction ConditionsOperation in experiment
73% Methyl-3-bromothiophene carboxylate (1.0 eq, 2.42 g, 10.95 mmol), <strong>[850568-47-7]2-amino-4-cyanophenylboronic acid hydrochloride</strong> (1.05 eq, 2.28 g, 11.49 mmol) and cesium carbonate (2.0 eq, 7.13 g, 21.9 mmol) were suspended in dioxane (25 ml) containing 5% water. The mixture was degassed by bubbling nitrogen for 10 minutes. PdCl2(dppf) (0.05 eq, 400 mg, 0.55 mmol) was added and the mixture was stirred at reflux for 1.5 hours. The mixture was cooled down, the solid filtered, washed with dioxane, water and methanol. After drying in vacuo, 4-oxo-4,5-dihydrothieno[2,3-c]quinoline-7-carbonitrile was isolated as a solid (1.81 g, 73% yield). LCMS (ES) m/z 227 [M+1]+.
  • 4
  • [ 76360-43-5 ]
  • [ 850568-47-7 ]
  • [ 1009827-27-3 ]
YieldReaction ConditionsOperation in experiment
48% With sodium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 120℃; for 0.166667h;Microwave irradiation; In a microwave vessel, methyl 2-bromo-3-thiophene carboxylate (1.0 eq, 250 mg, 1.13 mmol), 2-amino-3-cyanophenyl boronic acid HCl (1.1 eq, 250 mg, 1.24 mmol), sodium acetate (3.0 eq, 278 mg, 3.39 mmol) and PdCl2(dppf) (0.007 eq, 4.3 mg, 0.0082 mmol) were mixed together in anhydrous DMF (2.5 ml). The mixture was heated in a microwave oven at 120° C. for 10 nm. Water was added and the material extracted with CH2Cl2. The organic extracts were washed with brine, dried over Na2SO4 and the solvents removed in vacuo. The resulting solid was sonicated in AcOEt, filtered and dried to afford 4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carbonitrile as a beige solid (121 mg, 48percent yield). LCMS (ES): 95percent pure, m/z 227 [M+1]+.
  • 5
  • [ 16807-11-7 ]
  • [ 850568-47-7 ]
  • 3-amino-4-(9H-carbazol-1-yl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; ethanol; water; at 90.0℃; for 2h;Inert atmosphere; Microwave irradiation; A degassed stirred solution of 1-bromo-9H-carbazole (213 mg, 0.86 mmol, 1 eq), (2-amino-4-cyanophenyl)boronic acid.HCl (189 mg, 0.95 mmol, 1.1 eq), Na2CO3 (275 mg, 2.60 mmol, 3 eq) and Pd(PPh3)4 (50 mg, 0.043 mmol, 0.05 eq) in a mixture of 1,4-Dioxane:EtOH:H2O (2.5 mL, 2:1:1, 0.5 M) under an inert N2 atmosphere was heated with microwave irradiation at 90C for 2 h. Following completion the crude mixture was concentrated onto silica gel and purified by Isolera Biotage LPLC (CH/EA 8:2) to give 56b (72 mg, 29 %) as a red solid. vmax (cm-1) 3477, 3328, 2230, 1614, 1413, 1316, 1237, 752, 619; 1H-NMR (400 MHz, DMSO-d6): deltaH 10.79 (s, 1H), 8.02 - 8.33 (m, 2H), 7.50 (d, J = 8.07 Hz, 1H), 7.38 (dt, J = 1.04, 7.61 Hz, 1H), 7.24 - 7.33 (m, 3H), 7.21 (d, J = 1.59 Hz, 1H), 7.13 - 7.19 (m, 1H), 7.09 (dd, J = 1.71, 7.70 Hz, 1H), 5.19 (s, 2H); 13C-NMR (100 MHz CDCl3): deltaC 146.7, 140.1, 137.1, 131.7, 127.3, 126.0, 125.6, 123.1, 122.4, 120.8, 120.1, 120.0, 119.5, 119.2, 118.9, 118.7, 117.3, 111.4, 110.8; LR-ESI-MS: C19H14N3 [M+H]+ m/z found 284.05, cald 284.12.
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