Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | ||||||
{[ item.p_purity ]} | {[ item.pr_size ]} | Inquiry |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]} |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]} | {[ item.pr_usastock ]} | in stock Inquiry - | {[ item.pr_chinastock ]} | {[ item.pr_remark ]} in stock Inquiry - | Login | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
CAS No. : | 27257-15-4 | MDL No. : | MFCD09743451 |
Formula : | C8H8N2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | ZVOCBNCKNQJAFL-UHFFFAOYSA-N |
M.W : | 132.16 | Pubchem ID : | 583068 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
74% | b) 1-Methyl-lH-pyrrolo [2, 3-b] pyridine-3-carbaldehyde; POC13 (1.2 g, 7.9 mmol) was added dropwise with stirring to 10 mL of DMF at 0C. After stirring 10 min a solution of 1-methyl-lH-pyrrolo [2, 3-b] pyridine (0.95 g, 7. 2 mmol) in 5 mL of DMF was added during 1 min. The reaction mixture was stirred for lh at 0C and a further 30 min at 60C. It was poured into water which was made alkaline with NaHC03 (aq) and extracted 3 times with EtOAc. The combined organic layer was washed with water, dried over Na2SO4, filtered and evaporated. The crude product (0.85 g, 74%) was sufficiently pure to be used in the subsequent step below. 'H NMR (300 MHz, CDC13) No. 9. 97 (s, 1H), 8.55 (m, 1H), 8.44 (m, 1H), 7.84 (s, 1H), 7.27 (m, 1H), 3.97 (s, 3H). | |
9. 7-[2-(4-CYCLOBUTYLPIPERAZIN-l-YL)-2-OXOETHYL]-9-METHYL- 6,7,8,9-TETRAHYDRO-5H-PYRIDO[4',3':4,5]PYRROLO[2,3-B]PYRIDINE (SCHEME 7); Compound 9; Step 1. 1 -Methyl- 1 H-pyrro Io [2,3 -b]pyridine-3-carbaldehyde; <n="63"/>POCl3 (1.48 mL, 9.65 mmol) is added dropwise to a 0 0C solution of DMF (5 mL). The mixture is stirred 0.5 h at 0 0C. In a separate flask, 1 -methyl- IH- pyrrolo[2,3-b]pyridine (Journal of the American Chemical Society (2005) 127(22):8050-57; 1.04 g, 7.87 mmol) is dissolved in DMF (10 mL) and added dropwise to the first solution at 0 0C. The mixture is allowed to warm to rt and stirred overnight. The mixture is diluted with water (100 mL) and basified with IO N NaOH. The mixture is extracted with DCM (3 x 50 mL). The combined organic extracts are washed with water (3 x 100 mL) and brine (100 mL), dried over Na2SO4, and evaporated to yield the title compound. MS (+VE) m/z 161.12 (M+ +1). | ||
General procedure: POCl3 (5.87 ml, 63.0 mmol) was added dropwise to DMF (45 ml) at 0 C, and the mixture was stirred for 20 min at same temperature. A solution of 6-fluoro-1-methylindole (6.71 g, 45.0 mmol) in DMF (45 ml) was added slowly to the mixture at 0 C. After being stirred at room temperature for 1.5 h, the reaction mixture was poured into ice, and the resulting mixture was neutralized with 1 N NaOH and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, and concentrated to dryness. The residue was purified by column chromatography on silica gel with EtOAc as eluent to give the title compound (4.18 g, 52%) as a colorless solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With sodium hydrogencarbonate; trichlorophosphate; In ethyl acetate; N,N-dimethyl-formamide; | (Step 2) Synthesis of 1-methyl-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde Phosphoryl chloride (5.15 ml, 55.3 mmol) was added dropwise to DMF (70 ml) under stirring at 0?C. After the reaction mixture was stirred at 0?C for 10 minutes, a solution of 1-methyl-1H-pyrrolo(2,3-b)pyridine (4.87 g, 36.8 mmol) in DMF (5 ml) was added dropwise at the same temperature. After completion of the dropwise addition, the reaction mixture was stirred at 0?C for 4 hours and at 60?C for 3.5 hours. The reaction mixture was poured in ice water - a saturated aqueous solution of sodium bicarbonate to neutralize the mixture therewith, followed by extraction with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from ethyl acetate eluate fractions, 1-methyl-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde (4.87 g, 83%) was obtained as a yellow solid. 1H-NMR (CDCl3) delta: 3.98 (s, 3H), 7.28 (dd, J=7.8,4.7Hz, 1H), 7.85 (s, 1H), 8.44 (d, J=4.7Hz, 1H), 8.55 (d, J=7.8Hz, 1H), 9.97 (s, 1H). MS (ESI) m/z 160 (M+-H). |
47% | b) 1-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde According to the procedure of Preparation 40 (b), except substituting 1-methyl-1H-pyrrolo[2,3-b]pyridine (0.7 g, 5.3 mmole) for the 1,3-dimethylindole, the title compound (0.4 g, 47%) was prepared as a white solid: MS (ES) m/e 161 (M + H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With water; iodine; oxygen; sodium carbonate; In 1,4-dioxane; at 100℃; under 760.051 Torr; for 36h;Schlenk technique; Sealed tube; | General procedure: Under air, a 20 mL of Schlenk tube equipped with a stir bar was charged with indole 1 (0.2 mmol, 1 equiv),TMEDA (75 muL, 0.5 mmol, 2.5 equiv), Na2CO3 (42.4 mg, 0.4mmol, 2.0 equiv), 1,4-dioxane (0.5 mL) and H2O (100 muL). Then I2 (101.5 mg, 0.4 mmol, 2.0 equiv) was added and the tube was sealed with a rubber plug and charged with O2. The reaction mixture was stirred at 100 C for 36 h in oil bath. After cooling to room temperature, the resultant mixture was evaporated with EtOAc (20 mL) under reduced pressure and the residue was purified by flash column chromatography on a silica gel to give the products. |
[ 824-24-8 ]
4-Methyl-1H-pyrrolo[2,3-b]pyridine
Similarity: 0.95
[ 869335-48-8 ]
1-Methyl-1H-pyrrolo[2,3-b]pyridin-4-amine
Similarity: 0.92
[ 824-52-2 ]
5-Methyl-1H-pyrrolo[2,3-b]pyridine
Similarity: 0.92
[ 267876-25-5 ]
(1H-Pyrrolo[2,3-b]pyridin-5-yl)methanamine
Similarity: 0.90