| 68% |
|
Prepared according to GieBler et at. , Eur. ,/. Org. Chem 2010, 3611-3620. Methyl 3-( 1 //-pyrrol-2-yl)propanoate (780 mg, 4.84 mmol, 1.0 eq.) and 3,5-dimethyl- IH- pyrrole-2-carbaldehyde (690 mg, 5.32 mmol, 1.1 eq.) were dissolved in DCM (50 mL) and cooled to 0 C. To this mixture, a solution ofPOCl·, (500 pL, 5.36 mmol, 1.1 eq.) in DCM (5 mL) was added dropwise. The reaction mixture was stirred for 30 min at 0 C and for 6 h at room temperature. The resulting black solution was again cooled to 0 C and treated with BF3 x OEti (2.4 mL, 19.5 mmol, 4.0 eq.) and DIPEA (3.5 mL, 20.1 mmol, 4.2 eq.) and stirred for 12 h with gradual warming to room temperature. Then, the mixture was cooled to 0 C and water (100 mL) was added. The mixture was filtered through Celite which was rinsed with DCM (4 x 25 mL), the filtrate phases were separated and the aqueous layer was extracted with DCM (3 x 50 mL). The combined organic layers were dried with sodium sulfate and the solvents were removed under reduced pressure. The residue was absorbed on Celite and purified by column chromatography (eluent: 10-0% petroleum ether/DCM) to afford a red solid (1.00 g, 68% yield). NMR (400 MHz, CDCh): d 7.08 (s, 1 H), 6.88 (d, J = 3.4 Hz, 1 H), 6.26 (d, J = 3.6 Hz, 1 H), 6.1 1 (s, 1 H), 3.69 (s, 3 H), 3.29 (t, j= 7.6 Hz, 2 H), 2.77 (t, j= 7.6 Hz, 2 H), 2.56 (s, 3 H), 2.25 (s, 3 H). |
| 68% |
|
Prepared according to GieBler et a/., Eiir. J. Org. Chem 2010, 3611-3620. Methyl 3-( l //-pyrrol-2-yl)propanoate (780 mg, 4.84 mmol, 1.0 eq.) and 3, 5-dimethyl- 1 H- pyrrole-2-carbaldehyde (690 mg, 5.32 mmol, 1.1 eq.) were dissolved in DCM (50 mL) and cooled to 0 C. To this mixture, a solution ofPOCL (500 pL, 5.36 mmol, 1.1 eq.) in DCM (5 mL) was added dropwise. The reaction mixture was stirred for 30 min at 0 C and for 6 h at room temperature. The resulting black solution was again cooled to 0 C and treated with BF x OEti (2.4 mL, 19.5 mmol, 4.0 eq.) and DIPEA (3.5 mL, 20.1 mmol, 4.2 eq.) and stirred for 12 h with gradual warming to room temperature. Then, the mixture was cooled to 0 C and water (100 mL) was added. The mixture was filtered through Celite which was rinsed with DCM (4 x 25 mL), the filtrate phases were separated and the aqueous layer was extracted with DCM (3 x 50 mL). The combined organic layers were dried with sodium sulfate and the solvents were removed under reduced pressure. The residue was absorbed on Celite and purified by column chromatography (eluent: 10-0% petroleum ether/DCM) to afford a red solid (1.00 g, 68% yield). NMR (400 MHz, CDCh): d 7.08 (s, 1 H), 6.88 (d, j= 3.4 Hz, 1 H), 6.26 (d, ./= 3.6 Hz, 1 H), 6.11 (s, 1 H), 3.69 (s, 3 H), 3.29 (t, j= 7.6 Hz, 2 H), 2.77 (t, J= 7.6 Hz, 2 H), 2.56 (s, 3 H), 2.25 (s, 3 H). |
| 58% |
|
(0071) The BODIPY acid 11, used for preparing the azole fluorescent probes, was synthesized depicted in Scheme 2, following the procedure disclosed in Vanessa Saura et al. (2017). |
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