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[ CAS No. 131666-74-5 ]

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2D
Chemical Structure| 131666-74-5
Chemical Structure| 131666-74-5
Structure of 131666-74-5 *Storage: {[proInfo.prStorage]}

Quality Control of [ 131666-74-5 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 131666-74-5 ]

SDS

Product Details of [ 131666-74-5 ]

CAS No. :131666-74-5MDL No. :MFCD20527514
Formula :C10H10N2O2Boiling Point :-
Linear Structure Formula :-InChI Key :GJIMTGCSEXYRCB-UHFFFAOYSA-N
M.W :190.20Pubchem ID :14458625
Synonyms :

Computed Properties of [ 131666-74-5 ]

TPSA : 55 H-Bond Acceptor Count : 3
XLogP3 : 1.4 H-Bond Donor Count : 1
SP3 : 0.20 Rotatable Bond Count : 3

Safety of [ 131666-74-5 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 131666-74-5 ]

  • Upstream synthesis route of [ 131666-74-5 ]
  • Downstream synthetic route of [ 131666-74-5 ]

[ 131666-74-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 67-56-1 ]
  • [ 26663-42-3 ]
  • [ 131666-74-5 ]
YieldReaction ConditionsOperation in experiment
93% at 68℃; for 16.00 h; To a stirred solution of 2-(1H-indazol-3-yl)acetic acid (35-1) (4.86 g, 27.5 mmol) in Methanol (250 mL ) was added sulfuric acid (0.543 g, 5.53 mmol) and the reaction was refluxed at 68°C for 16 h. Reaction progress was monitored by TLC. The MeOH was evaporated to dryness and the residual gum was basified with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and evaporated in vacuo to yield methyl 2-(1H-indazol-3-yl)acetate (35-2) (4.90 g, 25.7 mmol, 93 percent) as a light brown solid.
77% for 14.00 h; Reflux General procedure: A solution of the (2-aza-)indoleacetic acid derivative (1 equivalent) in alcohol (preferentially methanol; 8.8 mL/mmol) containing 3 drops/mmol of concentrated sulfuric acid is refluxed overnight until the starting material is consumed. The progress of the conversion is monitored by TLC and/or LCMS. The reaction mixture is concentrated under reduced pressure to a low volume, and then diluted with ethyl acetate (5 mL/mmol). The organic layer is treated with water (2x3 mL/mmol) and 10percent sodium bicarbonate solution (3 mL). The ethyl acetate phase is collected, dried over sodium sulfate, concentrated and then kept at high vacuum to obtain the title compound as an amorphous solid.
Reference: [1] Patent: WO2017/197046, 2017, A1. Location in patent: Page/Page column 328
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7344 - 7350
[3] Tetrahedron, 2012, vol. 68, # 48, p. 10049 - 10058,10
[4] Tetrahedron, 2012, vol. 68, # 48, p. 10049 - 10058
[5] Tetrahedron, 2012, vol. 68, # 49, p. 10180 - 10187
[6] Patent: WO2013/59245, 2013, A1. Location in patent: Page/Page column 64
  • 2
  • [ 26663-42-3 ]
  • [ 131666-74-5 ]
Reference: [1] Patent: US4954629, 1990, A
[2] Patent: EP325375, 1989, A1
  • 3
  • [ 174180-42-8 ]
  • [ 131666-74-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7344 - 7350
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7344 - 7350
  • 4
  • [ 101714-15-2 ]
  • [ 131666-74-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7344 - 7350
  • 5
  • [ 67-56-1 ]
  • [ 26663-42-3 ]
  • [ 131666-74-5 ]
YieldReaction ConditionsOperation in experiment
93% at 68℃; for 16.00 h; To a stirred solution of 2-(1H-indazol-3-yl)acetic acid (35-1) (4.86 g, 27.5 mmol) in Methanol (250 mL ) was added sulfuric acid (0.543 g, 5.53 mmol) and the reaction was refluxed at 68°C for 16 h. Reaction progress was monitored by TLC. The MeOH was evaporated to dryness and the residual gum was basified with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and evaporated in vacuo to yield methyl 2-(1H-indazol-3-yl)acetate (35-2) (4.90 g, 25.7 mmol, 93 percent) as a light brown solid.
77% for 14.00 h; Reflux General procedure: A solution of the (2-aza-)indoleacetic acid derivative (1 equivalent) in alcohol (preferentially methanol; 8.8 mL/mmol) containing 3 drops/mmol of concentrated sulfuric acid is refluxed overnight until the starting material is consumed. The progress of the conversion is monitored by TLC and/or LCMS. The reaction mixture is concentrated under reduced pressure to a low volume, and then diluted with ethyl acetate (5 mL/mmol). The organic layer is treated with water (2x3 mL/mmol) and 10percent sodium bicarbonate solution (3 mL). The ethyl acetate phase is collected, dried over sodium sulfate, concentrated and then kept at high vacuum to obtain the title compound as an amorphous solid.
Reference: [1] Patent: WO2017/197046, 2017, A1. Location in patent: Page/Page column 328
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7344 - 7350
[3] Tetrahedron, 2012, vol. 68, # 48, p. 10049 - 10058,10
[4] Tetrahedron, 2012, vol. 68, # 48, p. 10049 - 10058
[5] Tetrahedron, 2012, vol. 68, # 49, p. 10180 - 10187
[6] Patent: WO2013/59245, 2013, A1. Location in patent: Page/Page column 64
  • 6
  • [ 26663-42-3 ]
  • [ 131666-74-5 ]
Reference: [1] Patent: US4954629, 1990, A
[2] Patent: EP325375, 1989, A1
  • 7
  • [ 174180-42-8 ]
  • [ 131666-74-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7344 - 7350
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7344 - 7350
  • 8
  • [ 101714-15-2 ]
  • [ 131666-74-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7344 - 7350
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