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CAS No. : | 1427366-38-8 | MDL No. : | MFCD23706323 |
Formula : | C10H8FNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YNCFIMKFPZAIMY-UHFFFAOYSA-N |
M.W : | 193.17 | Pubchem ID : | 122705880 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 49.54 |
TPSA : | 42.09 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) : | -6.06 cm/s |
Log Po/w (iLOGP) : | 1.93 |
Log Po/w (XLOGP3) : | 2.0 |
Log Po/w (WLOGP) : | 2.51 |
Log Po/w (MLOGP) : | 1.8 |
Log Po/w (SILICOS-IT) : | 2.77 |
Consensus Log Po/w : | 2.2 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.64 |
Solubility : | 0.441 mg/ml ; 0.00228 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.51 |
Solubility : | 0.596 mg/ml ; 0.00309 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.64 |
Solubility : | 0.0441 mg/ml ; 0.000228 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.61 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
5.3% | Stage #1: 4-isopropylthiazole-2-carbonyl chloride With aluminum (III) chloride In dichloromethane at 25℃; for 0.25h; Stage #2: methyl 7-fluoro-1H-indole-6-carboxylate In dichloromethane at 60℃; for 12h; | 1.2 Step 2: Methyl 7-fluoro-3-(4-isopropylthiazole-2-carbonyl)-1H-indole-6-carboxylate To a mixture of 4-isopropylthiazole-2-carbonyl chloride (240 mg, 1.27 mmol, N/A purity, 1 eq) in DCM (5 mL) was added AICE (1 g, 7.50 mmol, 5.93 eq) at 25 °C. The mixture was stirred at 25 °C for 0.25 h. Methyl 7-fluoro-l//-indole-6-carboxylate (200 mg, 897.64 pmol, 86.7% purity, 7.09e-l eq) was added. The mixture was stirred at 60 °C for 12 h. The reaction mixture was quenched with MeOH (30 mL) and concentrated under reduced pressure to yield a residue which was purified by flash silica gel chromatography (from PE/EtOAc = 100/1 to 2/1, TLC: PE/EtOAc = 2/1, Rf= 0.40) to yield methyl 7-fluoro-3-(4-isopropylthiazole-2-carbonyl)- l//-indole-6-carboxylate (23.01 mg, 66.43 pmol, 5.3% yield, 100.0% purity) as an off-white solid. NMR (500 MHz, CDCb) S ppm 9.31 (d, J= 3.2 Hz, 1H), 9.12 (s, 1H), 8.32 (d, 8.5 Hz, 1H), 7.88 (dd, J= 6.6, 8.3 Hz, 1H), 3.98 (s, 3H), 3.22 (td, J= 7.0, 13.7 Hz, 1H), 1.41 (d, J = 7.0 Hz, 6H); ES-LCMS m/z 347.1 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.5% | With thionyl chloride; N,N-dimethyl-formamide at 25℃; for 12h; | 1.1 Step 1 : Methyl 7-fluoro-1H-indole-6-carboxylate To a solution of 7-fluoro-l -indole-6-carboxylic acid (250 mg, 1.40 mmol, 1 eq) inDMF (0.01 mL) and MeOH (5 mL) was added SOCh (410.00 mg, 3.45 mmol, 0.25 mL, 2.47 eq) dropwise at 25 °C. The mixture was stirred at 25 °C for 12 h. TLC (PE/EtOAc = 2/1, Rf= 0.50) showed the starting material was consumed completely. The reaction mixture was concentrated under reduced pressure to yield a residue which was purified by flash silica gel chromatography (from PE/EtOAc = 100/1 to 5/1, TLC: PE/EtOAc = 2/1, Rf= 0.50) to yield methyl 7-fluoro-l//- indole-6-carboxylate (250 mg, 1.25 mmol, 89.5% yield, 96.5% purity) as a white solid. ^NMR (400 MHz, CDCh) d ppm 8.63 (br s, 1H), 7.66 (dd, J= 6.4, 8.3 Hz, 1H), 7.41 (d, J= 8.6 Hz,1H), 7.39 (t, J= 2.7 Hz, 1H), 6.64-6.60 (m, 1H), 3.96 (s, 3H); ES-LCMS m/z 194.3 [M+H]+ |
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