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CAS No. : | 6132-37-2 | MDL No. : | MFCD00092362 |
Formula : | C7H7BrO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GVAPLPBPJARJEY-UHFFFAOYSA-N |
M.W : | 219.03 | Pubchem ID : | 345282 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.29 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 42.49 |
TPSA : | 39.44 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.07 cm/s |
Log Po/w (iLOGP) : | 2.36 |
Log Po/w (XLOGP3) : | 2.21 |
Log Po/w (WLOGP) : | 2.22 |
Log Po/w (MLOGP) : | 1.13 |
Log Po/w (SILICOS-IT) : | 2.11 |
Consensus Log Po/w : | 2.01 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.73 |
Solubility : | 0.409 mg/ml ; 0.00187 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.67 |
Solubility : | 0.465 mg/ml ; 0.00212 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.95 |
Solubility : | 0.245 mg/ml ; 0.00112 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.43 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: With oxalyl dichloride In dichloromethane at 20℃; for 1 h; Stage #2: With triethylamine In dichloromethane for 15 h; |
To a stirred suspension of 5-bromo-2-furoic acid (15.0 g, 78.54 [MMOL)] in 225 mL of CH2CI2 at room temperature was added [OXALYL] chloride followed by a catalytic amount of N, N'-dimethylforamide. After 1 h, ethanol (20 mL) was added followed by [TRIETHYLAMINE (22 ML).] Reaction was continued for 15 h. The mixture was concentrated under reduced pressure to a residue, which was extracted with excess volume of hexanes, and [HEXANES-CH2CI2 (3] : 1, v/v). The extracts were filtered, the filtrated was concentrated to a yellow oil, dried on high vacuum, yielding 17.2 g (93percent) of the desired ester. |
93% | Stage #1: With oxalyl dichloride In dichloromethane at 20℃; for 1 h; Stage #2: With triethylamine In dichloromethane at 20℃; |
To a suspension of 5-bromo-2-furoic acid (15g) in CH2CI2 (275moi) at room temperature was added oxalyl chloride (6. 9ml) followed by a catalytic amount of N, N'- dimethylformamide (0.3ml). The mixture was stirred for 1 hr, whereupon, EtOH (20moi) and TEA (22ml) were added and then let stir overnight. The mixture was concentrated in vacuo and extracted with hexanes and hexanes/CH2CI2. The extracts were concentrated in vacuo to give an oil (17. 2g, 93percent). |
81% | at 80℃; for 12 h; | Compound 3 (5 . 37 g, 30 mmol) dissolved in 100 ml of ethanol in the solvent, by adding 2 ml of concentrated sulfuric acid, heated to 80 degree Celcius reflux reaction for 12 hours, concentrated under reduced pressure to remove the solvent, is added to the remaining reaction mixture in 100 ml of ice water, and saturated sodium carbonate solution to adjust the pH to 7 - 8, ethyl acetate extraction reaction solution three times, the combined organic phase after washing with saturated sodium chloride solution, dried with anhydrous sodium sulfate. The solvent is removed under reduced pressure, vacuum drying to obtain compound 4 b (5 . 32 g, 24.3 mmol), yield 81percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With oxalyl dichloride; triethylamine In dichloromethane at 20℃; for 15 h; | To a stirred suspension of 5-bromo-2-furoic acid (15.0 g, 78.54 mmol) in 225 mL of CH2Cl2 at room temperature was added oxalyl chloride followed by a catalytic amount of N,N?-dimethylforamide. After 1 h, ethanol (20 mL) was added followed by triethylamine (22 mL). Reaction was continued for 15 h. The mixture was concentrated under reduced pressure to a residue, which was extracted with excess volume of hexanes, and hexanes-CH2Cl2 (3:1, v/v). The extracts were filtered, the filtrated was concentrated to a yellow oil, dried on high vacuum, yielding 17.2 g (93percent) of the desired ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1 h; Stage #2: With triethylamine In dichloromethane for 15 h; |
To a stirred suspension of 5-bromo-2-furoic acid (15.0 g, 78.54 mmol) in 225 mL of CH2C12 at room temperature was added oxalyl chloride followed by a catalytic amount of N,N'-dimethylforamide. After 1 h, ethanol (20 mL) was added followed by triethylamine (22 mL). Reaction was continued for 15 h. The mixture was concentrated under reduced pressure to a residue, which was extracted with excess volume of hexanes, and hexanes-CH C12 (3:1, v/v). The extracts were filtered, the filtrated was concentrated to a yellow oil, dried on high vacuum, yielding 17.2 g (93percent) of the desired ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | Heating / reflux | Intermediate 1: S-Bromo-furan-l-carboxylic acid ethyl ester A solution of 5-bromofuran-2-carboxylic acid (2 g) in ethanol (15 ml) was treated with cone, sulphuric acid (2 drops) and heated to reflux overnight. The mixture was then <n="28"/>concentrated to dryness. The residue was partitioned between DCM (50 ml) and 2M NaHCO3. The DCM was separated, dried, and concentrated to dryness to afford an oil (1.6 g, 69percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate In N,N-dimethyl-formamide at 90℃; for 6 h; | Compound 4 b (10.0 g, 45.7 mmol) is dissolved in 100 ml of DMF in, by adding sodium bicarbonate (7 . 68 g, 18.3 mmol) and ethanol (42.0 g, 0.91 mol), add [1, 1' - double-(diphenyl phosphino) ferrocene] palladium dichloride (1 . 67 g, 2.28 mmol), the reaction system is put in stainless steel high-pressure in the reactor, agglomeration in polytetrafluoroethylene liner, maintain the temperature for a 90 degree Celcius, access 10 atmospheric pressure carbon monoxide, reaction 6 hours after the end of the, adding 200 ml of diluted with water and ethyl acetate extraction three times, combined with the organic phase, washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, through the simple concentration after column chromatography (ethyl acetate: petroleum ether=1:10, v: v), to obtain the product 5 b (9 . 21 g, 43.4 mmol), yield 95percent. |
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