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CAS No. : | 1173155-59-3 | MDL No. : | MFCD28952870 |
Formula : | C16H19BrN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DDUJJQUROUAQCF-UHFFFAOYSA-N |
M.W : | 351.24 | Pubchem ID : | 57950460 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
36% | Stage #1: tert-butyl 6-bromo-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate With sodium hydride In N,N-dimethyl-formamide for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide for 0.5h; | 46.d tert-Butyl 6-bromo-3,4-dihydro-lH-pyrido[3,4-6]indole-2(9H)-carboxylate (1.15 g, 3.26 mmol) was dissolved in DMF (20 mL) and sodium hydride (60% weight dispersion in mineral oil, 196 mg, 4.89 mmol) was added. After 1 h, methyl iodide (0.30 mL, 4.9 mmol) was added and the reaction mixture was stirred for a further 30 min. The mixture was diluted with methylene chloride and washed with 5% lithium chloride solution (5χ), dried Attorney's Docket 2882.023B over Na2SO4 and concentrated. Purification by flash column chromatography (silica gel, hexanes/ethyl acetate, 97:3 to 75:25) gave the title compound (740 mg, 36%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 7.58 (s, IH), 7.24 (d overlapped by solvent, J= 8.5, IH), 7.14 (d, J= 8.5, IH), 4.67-4.53 (br m, 2H), 3.79-3.67 (br m, 2H), 3.60 (s, 3H), 2.78- 2.66 (br m, 2H), 1.51 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | In tetrahydrofuran; dichloromethane for 2.5h; | 46.c 6-Bromo-2,3,4,9-tetrahydro-lH-pyrido[3,4-δ]indole (2.6 g, 10 mmol) was suspended in CH2Cl2 (50 mL) and THF (7.5 mL) and BoC2O (2.3 g, 11 mmol) was added. After 2.5 h, the mixture was concentrated. Purification by flash column chromatography (silica gel, hexanes/ethyl acetate, 97:3 to 70:30) gave the title compound (1.15 g, 30%) as an orange powder: 1H NMR (300 MHz, CDCl3) δ 7.59 (s, IH), 7.23 (d, J= 8.5 Hz, IH), 7.18 (d, J= 8.5 Hz, IH), 4.68-4.59 (br m, 2H), 3.80-3.70 (br m, 2H), 2.78-2.71 (br m, 2H), 1.50 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: tert-butyl 6-bromo-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.583333h; Cooling with ice; Stage #2: 1-(3-bromopropoxy)-4-chlorobenzene In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: tert-butyl 6-bromo-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.583333h; Stage #2: methyl 2-(4-(3-bromopropoxy)phenyl)acetate In N,N-dimethyl-formamide at 20℃; for 1h; |