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[ CAS No. 677306-38-6 ] {[proInfo.proName]}

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Product Details of [ 677306-38-6 ]

CAS No. :677306-38-6 MDL No. :MFCD03840644
Formula : C8H6N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :KGKZHHIUOZGUNP-UHFFFAOYSA-N
M.W : 162.15 Pubchem ID :21982323
Synonyms :

Safety of [ 677306-38-6 ]

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 [ 677306-38-6 ]

* 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.

  • Upstream synthesis route of [ 677306-38-6 ]
  • Downstream synthetic route of [ 677306-38-6 ]

[ 677306-38-6 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 677306-38-6 ]
  • [ 18107-18-1 ]
  • [ 192945-49-6 ]
YieldReaction ConditionsOperation in experiment
50% at 20℃; Synthesis of lH-Indazole-4-carboxylic acid methyl ester (18a): To a solution of lH-Indazole-4-carboxylic acid (lOOmg, 0.62 mmol) in 6 mL of methanol-dichloromethane (1 : 1) was added trimethylsilyl diazomethane (2.0 M in ethyl ether) dropwise at room temperature. More trimethylsilyl diazomethane was added until the starting material disappeared. Solvent was removed carefully and the residue was purified by column chromatography (50percent ethyl acetate/hexanes). The product (54 mg, 50percent) was obtained as a colorless solid. MS (ES) M+H expected = 177.1, found = 177.2.
Reference: [1] Patent: WO2007/51062, 2007, A2, . Location in patent: Page/Page column 127-128
[2] Patent: WO2011/49917, 2011, A1, . Location in patent: Page/Page column 42-43
[3] Patent: WO2009/134666, 2009, A1, . Location in patent: Page/Page column 50
  • 2
  • [ 186407-74-9 ]
  • [ 677306-38-6 ]
YieldReaction ConditionsOperation in experiment
55%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5 h;
Stage #2: With sec.-butyllithium In cyclohexane at -50℃; for 2 h;
Stage #3: for 1 h;
To a solution of bromoindazole (1.00 eqiv) in anhydrous tetrahydrofuran (7 L/mol) at room temperature was added sodium hydride (60percent in mineral oil, 1.11 eqiv) in several portions. The resulting solution was maintained for 30 min at room temperature and was then cooled to-60 C.A 1.3 M solution of sec-butyllithium in cyclohexane (2.1 eqiv) was added to the reaction mixture while maintaining the internal temperature below-50 C. The mixture was maintained for an additional 2 h at -50 C. A steady stream of anhydrous carbon dioxide was bubbled through the reaction mixture for 1 h. The flow was continued while the reaction mixture was allowed to warm to room temperature. Brine (6 L/mol) was added and the pH of the mixture was adjusted to 5 with concentrated hydrochloric acid. The mixture was extracted with warm ethyl acetate (3 x 8 L/mol) and the combined extracts were washed with small volume of brine, dried over anhydrous sodium sulfate, and concentrated. The product was purified by chromatography on silica gel or by crystallization
Reference: [1] Patent: WO2004/29050, 2004, A1, . Location in patent: Page 103;104
  • 3
  • [ 192945-49-6 ]
  • [ 677306-38-6 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: With sodium hydroxide In ethanol; waterHeating / reflux
Stage #2: With hydrogenchloride In water
A solution of sodium hydroxide (1.70 g, 42.6 mmol) in water (25 ml) was added to a solution of methyl 1H-indazole-4-carboxylate (Description 9,2. 50 g, 14.2 mmol) in ethanol (50 ml) and the resulting mixture heated at reflux overnight. The ethanol was removed from the cooled reaction mixture by evaporation and the aqueous phase then acidified by the addition of conc. HCI. The resultant precipitate was collected by filtration and dried under vacuum to give the title compound as an orange solid (2.0 g, 87percent). H NMR (400 MHZ, DMSO-D6) 8 7. 48 (lH, m), 7.81 (1H, dd, J7.4 and 0. 7), 7.85 (1H, dd, J 8. 4 and 0.8), 8.42 (1H, d, J0.8), 9.20 (1H, br s).
56%
Stage #1: With water; sodium hydroxide In methanol for 6 h; Reflux
Stage #2: With hydrogenchloride In waterCooling with ice
To a stirred solution of indazole-4-carboxylic acid methyl ester (0.3 g 1.7 mmol) in 10 mL methanol, NaOH (0.27 g, 6.8 mmol) in 2 mL of water was added and the reaction mixture was refluxed for 6 h. The reaction was cooled and the solvent was evaporated under reduced pressure and 2 mL of water was added. The solution was cooled on ice and compound was precipitated by adding concentrated HCl drop-wise. The resulting yellow precipitate was collected and washed with acidic water and dried (0.15 g, 56percent). m.p. 223-226° C. 1H NMR (400 MHz, DMSO-d6, TMS) δ 10.20 (bs, 2H), 7.75 (d, 1H), 7.60 (d, 1H), 7.35 (d, 1H), 7.28 (t, 1H).
Reference: [1] Patent: WO2005/28445, 2005, A2, . Location in patent: Page/Page column 29
[2] Patent: US2012/130078, 2012, A1, . Location in patent: Page/Page column 6
  • 4
  • [ 598-30-1 ]
  • [ 677306-38-6 ]
YieldReaction ConditionsOperation in experiment
30%
Stage #1: With sodium hydride In tetrahydrofuran at 20℃; for 0.5 h; Cooling with acetone-dry ice
Stage #2: at -50 - 50℃; for 2 h;
Stage #3: at -50℃; for 1 h;
To a cooled (water/ice bath) solution of bromomethylaniline (1.00 equiv. ) in chloroform (1.5 mL/mol) was added acetic anhydride (2.27 equiv. ) maintaining the temperature below 40 °C. The mixture was stirred at room temperature for 1 h. Potassium acetate (0.29 eq) was added followed by isoamyl nitrite (2.15 equiv. ). The reaction mixture was heated overnight to reflux. Volatiles were removed on vacuum rotary evaporator. Water (0.65 L/mol) was added to the residue and the mixture was again concentrated in vacuum. Hydrochloric acid (11 N, 1 L/mol) was added to the residue and the mixture was vigorously stirred and heated to 50°C for 2 h. The mixture was cooled to room temperature and pH was adjusted to 10 with 50percent aqueous sodium hydroxide while maintaining the temperature below 25 °C. The mixture was diluted with water (0.65 L/mol) and extracted with ethyl acetate (2 x 1.2 L/mol). The combined extracts were washed with brine (1 L/mol) and dried over anhydrous sodium sulfate. The organic solution was filtered through a plug of silica gel. The plug was further eluted with ethyl acetate. The solvent was removed on vacuum rotary evaporator, and the residue was triturated with heptane (1 L/mol). The solid material was collected by filtration, rinsed with heptane, and dried to provide the bromoindazole in 60-70percent yield. To a solution of the bromoindazole (1.00 equiv. ) in anhydrous THF (7 L/mol) was added sodium hydride (60percent in mineral oil, 1.11 equiv. ) in several portions at room temperature. The resulting solution was stirred 30 min at room temperature then cooled in dry ice/acetone bath. sec-Butyllithium (1.3 M in cyclohexane, 2.11 equiv. ) was added to the reaction mixture maintaining the temperature below -50 °C. The mixture was stirred 2 h at -50 °C. Anhydrous carbon dioxide was bubbled, through the reaction mixture at temperature below-40 °C for 1 h. The reaction was allowed to reach room temperature while keeping steady flow of carbon dioxide through the mixture. Brine (6 L/mol) was added and pH of the mixture was adjusted to 5 with concd. hydrochloric acid. The mixture was extracted with warm ethyl acetate (3 x 8 L/mol). The combined extracts were washed with small volume of brine, dried over anhydrous sodium sulfate and concentrated. The product was purified by chromatography on silica gel or by crystallization to provide the acid in 30-60percent yield. The acid was coupled with 1,4- diazabicyclo[3.2.2]nonane according to procedure A. The following acid was prepared by this method: 177-Indazole-4-carboxylic acid.
Reference: [1] Patent: WO2005/111038, 2005, A2, . Location in patent: Page/Page column 65-66
  • 5
  • [ 2258-42-6 ]
  • [ 186407-74-9 ]
  • [ 677306-38-6 ]
Reference: [1] Synthetic Communications, 2012, vol. 42, # 5, p. 658 - 666
  • 6
  • [ 18583-89-6 ]
  • [ 677306-38-6 ]
Reference: [1] Patent: US2012/130078, 2012, A1,
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