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Chemical Structure| 1015609-11-6 Chemical Structure| 1015609-11-6

Structure of 1015609-11-6

Chemical Structure| 1015609-11-6

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Product Details of [ 1015609-11-6 ]

CAS No. :1015609-11-6
Formula : C9H8N2O2
M.W : 176.17
SMILES Code : O=C(C1=CN=C2C(NC=C2)=C1)OC
MDL No. :MFCD09763671
InChI Key :JZFTWMGTLMPFEL-UHFFFAOYSA-N
Pubchem ID :11672756

Safety of [ 1015609-11-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1015609-11-6 ]

* 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 [ 1015609-11-6 ]

[ 1015609-11-6 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 1015609-11-6 ]
  • [ 1190322-95-2 ]
  • 2
  • [ 1015609-11-6 ]
  • [ 1190312-70-9 ]
YieldReaction ConditionsOperation in experiment
93% With N-chloro-succinimide; In N,N-dimethyl-formamide; at 20℃; To a 0 C. solution of <strong>[1015609-11-6]methyl 1H-pyrrolo[3,2-b]pyridine-6-carboxylate</strong> (1.00 g, 5.68 mmol) in N,N-dimethylformamide (15 mL) was added N-chlorosuccinimide (895 mg, 5.96 mmol). The reaction was allowed to gradually warm to room temperature and stir overnight. The reaction was diluted with water (125 mL) and stirred for 20 minutes. The resulting solid was collected by filtration, washed with water, and dried under vacuum to give the title compound (1.11 g, 93%) as an orange powder. +ESI (M+H) 211.0; 1H NMR (400 MHz, DMSO-d6, δ): 11.99 (br. s., 1H), 8.92 (d, J=2.0 Hz, 1H), 8.31 (d, J=1.8 Hz, 1H), 8.08 (d, J=3.1 Hz, 1H), 3.88 (s, 3H).
93% With N-chloro-succinimide; In N,N-dimethyl-formamide; at 0 - 20℃; Step 1: methyl 3-chloro-1H-pyrrolo[3,2-b]pyridine-6-carboxylate To a 0 C. solution of <strong>[1015609-11-6]methyl 1H-pyrrolo[3,2-b]pyridine-6-carboxylate</strong> (1.00 g, 5.68 mmol) in N,N-dimethylformamide (15 mL) was added N-chlorosuccinimide (895 mg, 5.96 mmol). The reaction was allowed to gradually warm to room temperature and stir overnight. The reaction was diluted with water (125 mL) and stirred for 20 minutes. The resulting solid was collected by filtration, washed with water, and dried under vacuum to give the title compound (1.11 g, 93%) as an orange powder. +ESI (M+H) 211.0; 1H NMR (400 MHz, DMSO-d6, δ): 11.99 (br. s., 1H), 8.92 (d, J=2.0 Hz, 1H), 8.31 (d, J=1.8 Hz, 1H), 8.08 (d, J=3.1 Hz, 1H), 3.88 (s, 3H).
  • 3
  • [ 5402-60-8 ]
  • [ 1015609-11-6 ]
  • methyl 1-(2,6-dimethylbenzyl)-1H-pyrrolo[3,2-b]pyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
21 mg With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 160℃; for 0.5h;Microwave irradiation; (1) Synthesis of methyl 1-(2,6-dimethylbenzyl)-1H-pyrrolo[3,2-b]pyridine-6-carboxyl ate [95-1] (hereinafter referred to as a compound [95-1]) To a solution of <strong>[1015609-11-6]methyl 1H-pyrrolo[3,2-b]pyridin-6-carboxylate</strong> (50 mg) in N-methyl-2-pyrrolidone (1 mL) were added potassium carbonate (158 mg) and 2,6-dimethylbenzyl chloride (91 mg), and then the reaction mixture was subj ected to microwave irradiation at 160C for 30 minutes. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (21 mg) as a white solid. 1H-NMR (400 MHz, CDCl3) δ: 9.14 (1H, s), 8.45 (1H, s), 7.25 (1H, t, J = 7.3Hz), 7.15 (2H, d, J = 7.3 Hz), 7.02 (1H, d, J = 3.0 Hz), 6.67 (1H, d, J = 3.0 Hz), 5.33 (2H, s), 4.00 (3H, s), 2.26 (6H, s). ESI-MS found: 295 [M+H]+
  • 4
  • [ 5402-60-8 ]
  • [ 1015609-11-6 ]
  • 1-(2,6-dimethylbenzyl)-1H-pyrrolo[3,2-b]pyridine-6-carboxylic acid [ No CAS ]
  • 5
  • [ 1015609-11-6 ]
  • Methyl 3-bromo-1-(5-fluoropyrimidin-2-yl)-1H-pyrrolo[3,2-b]pyridine-6-carboxylate [ No CAS ]
  • 6
  • [ 1015609-11-6 ]
  • Methyl 3-(3-(difluoromethoxy)phenyl)-1-(5-fluoropyrimidin-2-yl)-1H-pyrrolo[3,2-b]pyridine-6-carboxylate [ No CAS ]
  • 7
  • [ 1015609-11-6 ]
  • 3-(3-(Difluoromethoxy)phenyl)-1-(5-fluoropyrimidin-2-yl)-1H-pyrrolo[3,2-b]pyridine-6-carboxylic acid [ No CAS ]
  • 8
  • [ 1015609-11-6 ]
  • 3-(3-(difluoromethoxy)phenyl)-1-(5-fluoropyrimidin-2-yl)-N-((1R,2R)-2-morpholinocyclopentyl)-1H-pyrrolo[3,2-b]pyridine-6-carboxamide [ No CAS ]
  • 9
  • [ 947533-45-1 ]
  • [ 1015609-11-6 ]
  • Methyl 1-(5-fluoropyrimidin-2-yl)-1H-pyrrolo[3,2-b]pyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; In toluene; at 100℃; for 72.0h;Inert atmosphere; To a mixture of <strong>[1015609-11-6]methyl 1H-pyrrolo[3,2-b]pyridine-6-carboxylate</strong> (1.00 g, 5.68 mmol), 2-bromo-5-fluoropyrimidine (1.20 g, 6.81 mmol), K3PO4 (1.20 g, 5.68 mmol), (R,R)-N,N'-dimethylcyclohexane-1,2-diamine (0.323 g, 2.27 mmol) in toluene (57 mL) under N2 was added CuI (0.216 g, 1.13 mmol). The mixture was heated at 100 C. for 72 h. After cooling to RT, Celite was added, and the mixture was filtered and concentrated. The crude residue was purified by flash silica gel chromatography (0-100% EtOAc/hexanes) to afford the title compound. LC/MS=273 [M+1].
 

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[ 1015609-11-6 ]

Esters

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Related Parent Nucleus of
[ 1015609-11-6 ]

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