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CAS No. : | 1503-98-6 | MDL No. : | MFCD00029076 |
Formula : | C5H9NO | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | MFNYBOWJWGPXFM-UHFFFAOYSA-N |
M.W : | 99.13 | Pubchem ID : | 1274476 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P305+P351+P338 | UN#: | |
Hazard Statements: | H302-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% | With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 120℃; for 8h; | To a solution of 7-bromo-1 H-pyrrolo[2,3-c]pyridine (500 mg, 2.53 mmol) in toluene were added tris (dibenzylidene acetone) dipalladium (1 16.20 mg, 0.126 mmol), Xantphos (32.98 mg, 0.057 mmol), cesium carbonate (896 mg, 2.75 mmol), and cyclobutanecarboxamide (251 mg, 2.96 mmol, Intermediate 4). The resulting reaction mixture was heated to 120 C and stirred for 8 hours. After cooling to room temperature a saturated aqueous sodium bicarbonate solution (20 mL) was added to the reaction mixture and extracted with ethyl acetate (3 x 50 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel (100-200) column chromatography to afford A/-(1 /-/-pyrrolo[2,3-c]pyhdin-7-yl) cyclopropane carboxamide (200 mg, 36 % yield).1H NMR (400 MHz, CHCI3-cf): δ 7.72 - 7.79 (m, 1 H), 7.45 - 7.54 (m, 1 H), 7.38 - 7.45 (m, 1 H), 6.58 - 6.63 (m, 1 H), 3.47 - 3.51 (m, 1 H), 2.29 - 2.51 (m, 2H), 1 .88 - 2.14 (m, 2H), 1 .21 - 1 .31 (m, 2H). MS: 216.56 (M+1 ). |
36% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 120℃; for 8h; | To a solution of <strong>[165669-35-2]7-bromo-1H-pyrrolo[2,3-c]pyridine</strong> (500 mg, 2.53 mmol) in toluene were added tris (dibenzylidene acetone) dipalladium (116.20 mg, 0.126 mmol), Xantphos (32.98 mg, 0.057 mmol), cesium carbonate (896 mg, 2.75 mmol), and cyclobutanecarboxamide (251 mg, 2.96 mmol, Intermediate 4).; The resulting reaction mixture was heated to 120 C. and stirred for 8 hours. After cooling to room temperature a saturated aqueous sodium bicarbonate solution (20 mL) was added to the reaction mixture and extracted with ethyl acetate (3*50 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel (100-200) column chromatography to afford N-(1H-pyrrolo[2,3-c]pyridin-7-yl)cyclopropane carboxamide (200 mg, 36% yield). 1H NMR (400 MHz, CHCl3-d): δ 7.72-7.79 (m, 1H), 7.45-7.54 (m, 1H), 7.38-7.45 (m, 1H), 6.58-6.63 (m, 1H), 3.47-3.51 (m, 1H), 2.29-2.51 (m, 2H), 1.88-2.14 (m, 2H), 1.21-1.31 (m, 2H). MS: 216.56 (M+1). |
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