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CAS No. : | 22996-19-6 | MDL No. : | MFCD07779493 |
Formula : | C7H6BrNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VEVBVFGGMFKIBA-UHFFFAOYSA-N |
M.W : | 232.03 | Pubchem ID : | 15906236 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 49.09 |
TPSA : | 66.05 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) : | -6.61 cm/s |
Log Po/w (iLOGP) : | 1.21 |
Log Po/w (XLOGP3) : | 1.56 |
Log Po/w (WLOGP) : | 1.7 |
Log Po/w (MLOGP) : | 1.1 |
Log Po/w (SILICOS-IT) : | 0.2 |
Consensus Log Po/w : | 1.16 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.5 |
Solubility : | 0.735 mg/ml ; 0.00317 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.56 |
Solubility : | 0.643 mg/ml ; 0.00277 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.47 |
Solubility : | 0.792 mg/ml ; 0.00341 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.01 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
78% | With manganese(IV) oxide In dichloromethane at 20℃; for 12 h; | Step 2. 4-Bromo-2-nitrobenzaldehydeManganese (IV) oxide (4eq) was added to a 0.18M solution of (4-bromo-2-nitrophenyl)methanol in dichloromethane. The suspension was stirred at ambient temperature under Argon for 12 h. The reaction mixture was filtered through celite and filter cake was washed with dichloromethane. The combined filtrate was concentrated to give brown color solid in 78percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | Stage #1: With borane-THF In tetrahydrofuran at 20℃; for 72 h; Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran |
Step 1. Borane tetrahydrofuran complex solution (1 M in tetrahydrofuran, 13 mL, 13 mmol) was added over 5 min to a solution of 4-bromo-2-nitrobenzoic acid (2.00 g, 8.13 mmol) at room temperature, then after 72 h the reaction mixture was carefully poured upon sat. aq. sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was dried (MgSO4) and evaporated to produce (4-bromo-2-nitro-phenyl)-methanol (1.85 g, 96percent). White solid, 1H-NMR (300 MHz, CDCl3): 8.25 (d, J=1.8, 1H), 7.80 (dd, J=8.1, 1.8, 1H), 7.67 (d, J=8.1, 1H), 4.96 (d, J=6.3, 2H), 2.37 (t, J=6.3, 1H). |
95% | Stage #1: With borane In tetrahydrofuran at 0 - 20℃; for 48 h; Stage #2: With methanol In tetrahydrofuran at 0℃; |
Example 25 Synthesis of 4-(7-( 1 -isobutyl- 1 H-pyrazol-4-yl)quinazolin-2-ylamino)-N-(3-(pyrrolidin- 1 - yl)propyl)benzenesulfonamide (Compound 709)Stepl. (4-Bromo-2-nitrophenyl)methanolTo a 0.5M suspension of 4-bromo-2-nitrobenzoic acid in THF in an ice bath was slowly added borane (1.0M /THF, 4eq). The reaction mixture was stirred at ambient temperature for 48 h. LCMS showed the reaction was complete. The mixture was recooled to 00C and quenched with methanol and concentrated to remove solvent. The residue was taken into ethyl acetate and organic phase was washed with water, saturated sodium bicarbonate, brine, dried over sodium sulfate and concentrated to give yellow solid in 95percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium tetrahydroborate In ethanol; water at 0℃; for 17.5 h; | Preparation of Compound 217, (4-bromo-2-nitrophenyl)methanol [00300] To a stirring suspension of 4-bromo-2-nitrobenzaldehyde (550 mg, 2.391 mmol) in ethanol (14 mL) and water (7 mL) at 0 °C was added sodium borohydride (452 mg, 1 1 .96 mmol) and the reaction left to stir at 0 °C for 17.5 h. The reaction was diluted with water (30 ml), and extracted with EtOAc (2 x 30 ml) - brine was added to clear. The combined organic layer was washed with brine (30 ml), dried (MgS04) and concentrated in vacuo to afford the title compound as a yellow solid (536 mg, 97percent).1H NMR (500 MHz, Chloroform-d) δ 8.27 (d, J = 2.0 Hz, 1 H), 7.82 (dd, J = 8.3, 2.0 Hz, 1 H), 7.69 (d, J = 8.3 Hz, 1 H), 4.98 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With N-Bromosuccinimide; triphenylphosphine In N,N-dimethyl-formamide for 0.0333333 h; | Example 5; Synthesis of (3R)-3-amino-7-bromo-1-hydroxy-3,4-dihydroquinolin-2(1H)-one (29); 4-Bromo-1-(bromomethyl)-2-nitrobenzene (23); To a stirred solution of (4-bromo-2-nitrophenyl)methanol (22) (1.00 g, 4.31 mmol) in DMF (40 mL) was added NBS (1.6 g, 9.0 mmol) and triphenylphosphine (2.4 g, 9.2 mmol). After two minutes, the reaction mixture was concentrated in vacuo. The residue was partitioned between water and DCM, and the aqueous layer was extracted with additional DCM. The combined organic layers were concentrated and the residue was purified by silica gel chromatography (Gradient: 0percent to 20percent EtOAc in heptane) to provide the product (880 mg, 69percent). 1H NMR (400 MHz, CDCl3) δ 4.78 (s, 2H), 7.47 (d, J=8.2 Hz, 1H), 7.75 (dd, J=8.2, 2.1 Hz, 1H), 8.20 (d, J=2.1 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With iron; ammonium chloride In ethanol; water at 75℃; for 1 h; | Step 2. A mixture of (4-bromo-2-nitro-phenyl)-methanol (1.85 g, 7.97 mmol), iron powder (2.23 g, 39.9 mmol), ammonium chloride (213 mg, 3.99 mmol), ethanol (20 mL), and water (10 mL) was heated at 75° C. for 1 h, then after cooling filtered through a pad of diatomaceous earth. The filtrate was evaporated and the residue partitioned between ethyl acetate and water, the organic layer was washed with brine, dried (MgSO4), and evaporated to produce (2-amino-4-bromo-phenyl)-methanol (1.53 g, 90percent). Off-white solid, MS (EI)=201.0 (M+). |
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