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Chemistry
Heterocyclic Building Blocks
Indazoles
5-Methoxy-1-methylindazole
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Indazoles
Ethers

[ CAS No. 756839-44-8 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 756839-44-8
Chemical Structure| 756839-44-8
Structure of 756839-44-8 *Storage: {[proInfo.prStorage]}

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SDS

Product Details of [ 756839-44-8 ]

CAS No. :756839-44-8MDL No. :MFCD22380221
Formula : C9H10N2O Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :162.19Pubchem ID :-
Synonyms :

Computed Properties of [ 756839-44-8 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 756839-44-8 ]

Signal Word:Class
Precautionary Statements:UN#:
Hazard Statements:Packing Group:

Application In Synthesis of [ 756839-44-8 ]

  • Downstream synthetic route of [ 756839-44-8 ]

[ 756839-44-8 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 98-03-3 ]
  • [ 756839-44-8 ]
  • 5-(5-methoxy-1-methyl-1H-indazol-3-yl)thiophene-2-carbaldehyde [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2020,vol. 85,p. 1009 - 1021
  • 2
  • [ 756839-44-8 ]
  • [ 141-32-2 ]
  • butyl (E)-3-(5-methoxy-1-methyl-1H-indazol-3-yl)acrylate [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2020,vol. 85,p. 1009 - 1021
  • 3
  • [ 756839-44-8 ]
  • 1-[4-(5-methoxy-1-methyl-1H-indazol-3-yl)phenyl]-3-oxazol-5-ylmethylurea [ No CAS ]
Reference： [1]Patent: WO2018/132372,2018,A1
  • 4
  • [ 756839-44-8 ]
  • C16H13N3O2 [ No CAS ]
Reference： [1]Patent: WO2018/132372,2018,A1
  • 5
  • [ 756839-44-8 ]
  • 4-(5-methoxy-1-methyl-1H-indazol-3-yl)phenylamine [ No CAS ]
Reference： [1]Patent: WO2018/132372,2018,A1
  • 6
  • [ 756839-44-8 ]
  • 3-iodo-5-methoxy-1-methyl-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 80.0℃; To a solution of <strong>[756839-44-8]5-methoxy-1-methyl-1H-indazole</strong> (476 mg, 2.9 mmol) in DIVIF (10 mL) was added KOH (195 mg, 3.5 mmol) and 12(889 mg, 3.5 mmol). The resultant mixture was stirred at 80 C overnight. The reaction was quenched with the addition of saturated aqueous NaHSO3 (100 mL). The mixture was extracted with EA ( 30 mL x3). The combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated to dryness under reduced pressure. The residue was purified by silica gel column (PE/EA = 8/1) to give 3-iodo-<strong>[756839-44-8]5-methoxy-1-methyl-1H-indazole</strong> (580 mg, yield: 69%) as a white solid.
Reference： [1]Patent: WO2018/132372,2018,A1.Location in patent: Paragraph 01269
  • 7
  • [ 15579-15-4 ]
  • [ 74-88-4 ]
  • [ 756839-44-8 ]
YieldReaction ConditionsOperation in experiment
54% With potassium carbonate; In N,N-dimethyl-formamide; at 120.0℃; for 18.0h; To a solution of 1H-Jndazol-5-ol (1.3 g, 10 mmol) in DIVIF (40 mL) was added K2C03 (3.5 g, 25 mmol) and CH3I (1.6 mL, 25 mmol) at room temperature, the resulting mixture was stirred at 120 C for 18 hrs. After cooled to room temperature, the reaction was acidified with the addition of saturated aqueous NH4C1 (10 ml). The solvent was removed under vacuum and the residue was diluted with water (200 mL). The aqueous phase was extracted with EA (50 mL x3). The combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated to dryness under reduced pressure. The residue was purified by silica gel column (PE/EA = 4/1) to give 5-methoxy-1- methyl-1H-indazole (876 mg, yield: 54%) as a white solid. ?H NIVIR (300 IVIHz, CDC13): oe = 7.87 (s, 1H), 7.28 (d, J= 7.2 Hz, 1H), 7.08-7.05 (m, 2H), 4.04 (s, 3H), 3.84 (s, 3H). MS: m/z 163.0 (M+W).
Reference： [1]Patent: WO2018/132372,2018,A1.Location in patent: Paragraph 01268
  • 8
  • [ 756839-44-8 ]
  • [ 756839-14-2 ]
YieldReaction ConditionsOperation in experiment
AlCl3; In toluene; Step B: 1-Methyl-1H-indazol-5-ol (3t): To a solution of (2t) (0.99 g, 6.1 mmol) in toluene (30 mL) was added AlCl3 (2.44 g, 18.3 mmol) at room temperature, upon which a purple colored mixture formed. After refluxing for 20 minutes, an olive colored mixture formed. The mixture was refluxed for 2 hours, allowed to cool to room temperature and poured into an ice-water bath. The insoluble solids were collected by filtration (398 mg). The filtrate was extracted with DCM, filtered through IPS paper, evaporated in vacuo and purified on the Biotage eluding with (1:9) then (3:7) Et2O/DCM and finally (1:1) DCM/Et2O. The product fractions were evaporated in vacuo affording compound (3t) as a brown foam (122 mg). Total combined yield, 520 mg (58%). 1H NMR (400 MHz, CDCl3) delta 7.38 (d, J=7.8 Hz, 1H), 7.17 (dd, J=7.8, 1.6 Hz, 1H), 7.13 (d, J=1.6 Hz, 1H), 5.19-5.18 (m, 1H), 4.51-4.44 (m, 1H), 4.43-4.36 (m, 1H), 2.53-2.45 (m, 1H), 2.36-2.30 (m, 1H); MS (ESI+) m/z 149 (M+H) detected.
AlCl3; In toluene; Step B: 1-Methyl-1H-indazol-5-ol (3t): To a solution of (2t) (0.99 g, 6.1 mmol) in toluene (30 mL) was added AlCl3 (2.44 g, 18.3 mmol) at room temperature, upon which a purple colored mixture formed. After refluxing for 20 minutes, an olive colored mixture formed. The mixture was refluxed for 2 hours, allowed to cool to room temperature and poured into an ice-water bath. The insoluble solids were collected by filtration (398 mg). The filtrate was extracted with DCM, filtered through 1PS paper, evaporated in vacuo and purified on the Biotage eluding with (1:9) then (3:7) Et2O/DCM and finally (1:1) DCM/Et2O. The product fractions were evaporated in vacuo affording compound (3t) as a brown foam (122 mg). Total combined yield, 520 mg (58%). 1H NMR (400 MHz, CDCl3) delta 7.38 (d, J=7.8 Hz, 1H), 7.17 (dd, J=7.8, 1.6 Hz, 1H), 7.13 (d, J=1.6 Hz, 1H), 5.19-5.18 (m, 1H), 4.51-4.44 (m, 1H), 4.43-4.36 (m, 1H), 2.53-2.45 (m, 1H), 2.36-2.30 (m, 1H); MS (ESI+) m/z 149 (M+H) detected.
Reference： [1]Patent: US2004/180896,2004,A1
[2]Patent: US2004/192653,2004,A1

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