Alternatived Products of [ 27613-34-9 ]
Product Details of [ 27613-34-9 ]
CAS No. : | 27613-34-9 |
MDL No. : | MFCD18394296 |
Formula : |
C9H7NO
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
145.16
|
Pubchem ID : | - |
Synonyms : |
|
Application In Synthesis of [ 27613-34-9 ]
* 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 [ 27613-34-9 ]
- 1
-
[ 93340-34-2 ]
-
[ 27613-34-9 ]
Yield | Reaction Conditions | Operation in experiment |
86% |
With hydrogenchloride; Methyl fluorosulfonate; sodium tetrahydroborate CH2Cl2, 25 deg C, 15 hrs then EtOH-THF, from 0 deg C to 25 deg C, 30 min then 25 deg C, 20 min (one-pot); |
|
- 2
-
[ 80762-49-8 ]
-
[ 27613-34-9 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 57 percent / n-butyllithium, LDA, ethanol / diethyl ether; pentane / 0.75 h / -78 deg C, then 25 deg C, 45 min
2: 86 percent / FSO3Me, sodium borohydride, 4.5N HCl / CH2Cl2, 25 deg C, 15 hrs then EtOH-THF, from 0 deg C to 25 deg C, 30 min then 25 deg C, 20 min (one-pot) |
|
- 3
-
[ 27613-34-9 ]
-
3-formyl-2-methyl-5-nitrobenzonitrile
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
82% |
With sulfuric acid; nitric acid at 20℃; for 36h; Cooling with ice; |
|
- 4
-
[ 1192873-43-0 ]
-
[ 27613-34-9 ]
-
C40H31N5
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 3h; |
5.3.28 3-[[[3-(4-Pyridyl)-1H-indazol-5-yl]amino]methyl]benzonitrile [30]
General procedure: To a vial equipped with stir-bar was added intermediate 57 (69mg, 0.15mmol), 3-formylbenzonitrile (20mg, 0.15mmol) and DCM (0.61mL). The reaction was stirred vigorously at room temp before sodium triacetoxyborohydride (162mg, 0.76mmol) was added portion-wise and the resulting mixture was left to stir for 3h at room temp. Once no further conversion was observed via TLC, the reaction was concentrated and dissolved again in minimal DCM before triethylsilane (0.05mL, 0.31mmol) and TFA (0.5mL, 6.53mmol) were added. The mixture was vigorously stirred for 2h before the mixture was neutralized with TEA and extracted with 3 [Math Processing Error] × EtOAc and the organic phases combined and concentrated and purified by reverse phase FCC (12g C18, 0-100% MeOH in water). Fractions containing product were combined and concentrated and purified by normal phase FCC (5g SiO2, 0-5% MeOH in EtOAc) to give a yellow glass. Upon the addition of cold MeOH a precipitate formed which was filtered off and the filtrate was concentrated to give the product as a yellow solid (29mg, 56% over two steps). |
|
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 3h; |
5.3.28 3-[[[3-(4-Pyridyl)-1H-indazol-5-yl]amino]methyl]benzonitrile [30]
General procedure: To a vial equipped with stir-bar was added intermediate 57 (69mg, 0.15mmol), 3-formylbenzonitrile (20mg, 0.15mmol) and DCM (0.61mL). The reaction was stirred vigorously at room temp before sodium triacetoxyborohydride (162mg, 0.76mmol) was added portion-wise and the resulting mixture was left to stir for 3h at room temp. Once no further conversion was observed via TLC, the reaction was concentrated and dissolved again in minimal DCM before triethylsilane (0.05mL, 0.31mmol) and TFA (0.5mL, 6.53mmol) were added. The mixture was vigorously stirred for 2h before the mixture was neutralized with TEA and extracted with 3 [Math Processing Error] × EtOAc and the organic phases combined and concentrated and purified by reverse phase FCC (12g C18, 0-100% MeOH in water). Fractions containing product were combined and concentrated and purified by normal phase FCC (5g SiO2, 0-5% MeOH in EtOAc) to give a yellow glass. Upon the addition of cold MeOH a precipitate formed which was filtered off and the filtrate was concentrated to give the product as a yellow solid (29mg, 56% over two steps). |
Reference:
[1]Fitch, William L.; Gajera, Chandresh R.; Lam, Grace; Leśniak, Robert K.; Montine, Thomas J.; Nguyen, Khanh C.; Nichols, R. Jeremy; Schonemann, Marcus; Smith, Mark; Zhao, Jing
[European Journal of Medicinal Chemistry, 2022, vol. 229]
[2]Fitch, William L.; Gajera, Chandresh R.; Lam, Grace; Leśniak, Robert K.; Montine, Thomas J.; Nguyen, Khanh C.; Nichols, R. Jeremy; Schonemann, Marcus; Smith, Mark; Zhao, Jing
[European Journal of Medicinal Chemistry, 2022, vol. 229]