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CAS No. : | 17288-53-8 | MDL No. : | MFCD09038907 |
Formula : | C8H8N2O | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | CCNJNELOBGXDFD-UHFFFAOYSA-N |
M.W : | 148.16 | Pubchem ID : | 641092 |
Synonyms : |
|
Chemical Name : | 5-Methoxy-1H-pyrrolo[2,3-c]pyridine |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302 | 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 |
---|---|---|
In DMF (N,N-dimethyl-formamide);Heating / reflux; | [0546] 5-Methoxy-1H-pyrrolo [2,3-c] pyridine-3-carbaldehyde can be prepared from 165 using with 1,3, 5,7-tetraaza-adamantane under refluxing conditions with DMF (D. Mazeas et. al, Heterocycles, 1999,50, 1065-80). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; In DMF (N,N-dimethyl-formamide); | [0545] 5-Methoxy-lH-pyrrolo [2,3-c] pyridine 164 can be prepared through cyclization of 6-METHOXY-4-TRIMETHYLSILANYLETHYLNYL-PYRIDIN-3-YLAMINE 163 with cuprous iodide in DMF (D. Mazeas et. al, Heterocycles, 1999,50, 1065-80). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 1: Preparation of intermediate 164, 5-Methoxy-1H-pyrrolo[2,3-c]pyridine 5-Methoxy-1H-pyrrolo[2,3-c]pyridine 164 can be prepared through cyclization of 6-methoxy-4-trimethylsilanylethylnyl-pyridin-3-ylamine 163 with cuprous iodide in DMF (D. Mazeas et. al, Heterocycles, 1999, 50, 1065-80). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N,N-dimethyl-formamide dimethyl acetal;palladium; In ethanol; ethyl acetate; | A solution of 2-methoxy-4-methyl-5-nitropyridine (4.30 g, 25.57 mmol) and dimethylformamide dimethylacetal (35 ml) was heated at reflux under nitrogen for 40 hours. Ethyl acetate was added to this solution (150 ml), and this mixture was washed with water (150 ml). The aqueous extract was back-extracted with ethyl acetate (100 ml), and the organic extracts were combined, dried (Na2 O4), and evaporated under reduced pressure to yield a purple solid. The solid was dissolved in absolute ethanol (200 ml), and 5% palladium on carbon (3.0 g) was added to this solution which was shaken under a hydrogen atmosphere (3 atm) for 3 hours. The resultant reaction mixture was filtered, and the filtrate was evaporated under reduced pressure. Flash chromatography of the residue yielded compound 9 (2.05 g, 13.84 mmol, 54% last step, 50% overall) as a white crystalline solid: mp, 123-124 C.; IR (KBr) 1625, 1580, 1490, 1460, 1320, 1150 cm-1; 1 H NMR (DMSO-d6) delta 11.28 (br s, 1H), 8.37 (s, 1H), 7.57 (t, J=2.8 Hz, 1H), 6.86 (s, 1H), 6.33 (br m, 1H), 3.82 (s, 3H); 13 C NMR (DMSO-d6) delta 157.2, 136.4, 131.5, 130.7, 130.0, 99.6, 96.8, 53.4; LRMS (m/z, relative intensity) 149 (20), 148 (M+, 98), 147 (100), 119 (46), 118 (79), 117 (26), 105 (31), 91 (15), 70 (16); HRMS calculated for C8 H8 N2 O:148.0657, found: 148.0613. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With thionyl chloride; In N-methyl-acetamide; dichloromethane; toluene; | EXAMPLE 12 5-Methoxypyrrolo[2,3-c]pyridine (Compound 9) A mixture of 4-methyl-5-nitro-1H-pyridine-2-one (5.00 g, 32.44 mmol), thionyl chloride (20 ml), and two drops of dimethylformamide was heated atreflux under nitrogen for 52 hours. The resultant orange colored solution was evaporated under reduced pressure, and a small amount of anhydrous toluene was added and then removed via evaporation under reduced pressure to remove traces of thionyl chloride. The residual oil then passed througha silica gel filter (dried at 150 C. under vacuum overnight, approximately 100 g) followed by methylene chloride (1 1). This filtrate was evaporated under reduced pressure to afford 2-chloro-4-methyl-5-nitropyridine (5.30 g, 30.71 mmol, 95%) as an orange oil, which crystallized below 0 C.; IR (CHCl3) 1605, 1550, 1520, 1450, 1360, 1345 cm-1; 1 H NMR (CDCl3) delta 9.03 (s, 1H), 7.83 (s, 1H), 2.60 (s, 3H); LRMS (m/z, relative intensity) 174 (25), 173 (19), 172 (M+, 68), 157 (74), 155 (100), 128 (27), 101 (47), 100(55], 99 (74), 90 (43), 75 (36). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;copper acetylacetonate; In dimethyl sulfoxide; at 130℃; for 10h; | To a mixture of <strong>[17288-53-8]5-methoxy-1H-pyrrolo[2,3-c]pyridine</strong> (6.00 g, 40.5 mmol; cf. D.Mazeas et al., Heterocycles 50 (1999), 1065), copper(ll) acetylacetonate (1.06 g, 4.05 mmol) and potassium carbonate (11.2 g, 81.0 mmol) in DMSO (63 ml) was added iodobenzene (4.99 ml, 44.6 mmol). The reaction mixture was stirred at 130 0C for 10 h. The mixture was then cooled to room temperature, and a solution of ammonium chloride (20 % in water) was added. The mixture was filtered through celite and the filtrate extracted three times with EA. The organic layers were combined, dried over sodium sulfate, filtered and evaporated under reduced pressure. <n="90"/>Column chromatography of the residue on silica gel (EA/HEP) gave 8.43 g of the title compound.LC/MS (method LC4): m/z = 225 |
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