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CAS No. : | 1190322-18-9 | MDL No. : | MFCD12962862 |
Formula : | C7H6BrN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SMKKFZYQAFGAIC-UHFFFAOYSA-N |
M.W : | 212.05 | Pubchem ID : | 53413015 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 48.2 |
TPSA : | 54.7 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) : | -6.41 cm/s |
Log Po/w (iLOGP) : | 1.42 |
Log Po/w (XLOGP3) : | 1.66 |
Log Po/w (WLOGP) : | 1.92 |
Log Po/w (MLOGP) : | 1.54 |
Log Po/w (SILICOS-IT) : | 1.99 |
Consensus Log Po/w : | 1.71 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.81 |
Solubility : | 0.332 mg/ml ; 0.00156 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.42 |
Solubility : | 0.802 mg/ml ; 0.00378 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.41 |
Solubility : | 0.0823 mg/ml ; 0.000388 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.69 |
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 |
---|---|---|
Multi-step reaction with 2 steps 1.1: 3-chloro-benzenecarboperoxoic acid / diethyl ether / 5 h / 0 - 20 °C / Inert atmosphere 2.1: dimethyl sulfate / acetonitrile / 8 h / 80 °C / Inert atmosphere 2.2: 48 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
570 mg | Stage #1: 5-bromo-7-oxido-1H-pyrrolo[2,3-b]pyridin-7-ium With dimethyl sulfate In acetonitrile at 80℃; for 8h; Inert atmosphere; Stage #2: With ammonia In methanol; acetonitrile at 20℃; for 48h; Inert atmosphere; | 9.2 Step 2: Preparation of 5-bromo-1H-pyrrolo[2,3-b]pyridine-6-amine (70) Step 2: Preparation of 5-bromo-1H-pyrrolo[2,3-b]pyridine-6-amine (70) (0898) A suspension solution of the intermediate 69 in anhydrous ACN (10 mL) was added with dimethylsulfate (0.5 mL, 5.25 mmol). The reaction mixture was stirred at 80° C. for 8 hours and cooled to 0° C. The resulting reaction mixture was added with an ammonia solution (10 mL, 7N in MeOH), stirred at 60° C. for 2 days under nitrogen conditions, and the solvent was removed therefrom under reduced pressure. The residue was dissolved in ethyl acetate, and then washed with a saturated Na2CO3 solution and brine. The organic layer was evaporated and purified by silica gel column chromatography to give the intermediate 70 (570 mg, 54%). (0899) [M+H]+ 212 and 214. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium methylate / methanol / 6 h / 120 °C / Inert atmosphere 2: hydrogenchloride / methanol / 16 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium methylate / methanol / 6 h / 120 °C / Inert atmosphere 2: hydrogenchloride / methanol / 16 h / Inert atmosphere 3: triethylamine / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: sodium methylate / methanol / 6 h / 120 °C / Inert atmosphere 2: hydrogenchloride / methanol / 16 h / Inert atmosphere 3: triethylamine / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere 4: caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,2-dimethoxyethane; water / 3 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium methylate In methanol at 120℃; for 6h; Inert atmosphere; | 9.3 Step 3: Preparation of tert-butyl 4-(6-amino-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (71) Step 3: Preparation of tert-butyl 4-(6-amino-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (71) (0900) A solution of the intermediate 70 (400 mg, 1.89 mmol) and 1-Boc-4-piperidone (752 mg, 3.77 mmol, 2.0 eq) in MeOH (2.4 mL) was added with NaOMe (2.4 mL, 25% MeOH solution). Then, the mixture was heated to 120° C. and stirred for 6 hours at the above temperature. Subsequently, the resulting mixture was added to ice water (50 mL), extracted with EtOAc (2×100 mL), washed with a saturated NaCl solution (50 mL), dried over anhydrous MgSO4 and concentrated to give the crude product, which was then crystallized from N-hexane/EtOAc (v/v=10:1) (50 mL) to give the crude intermediate 71 (651 mg, 1.66 mmol, 88%) as a yellow solid. (0901) [M+H]+ 393 and 395. |
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