Table 1.
Entry | Nomenclature | X | Y | Yield (%) 2 |
---|---|---|---|---|
1 | 8a | CH2 | H | 50 |
2 | 8b | N-Boc | H | 70 |
3 | 8c | O | H | 43 |
4 | 8d | S | H | 82 |
5 | 8e | CH2 | F | 19 |
6 | 8f | N-Boc | F | 62 |
7 | 8g | O | F | 52 |
8 | 8h | S | F | 42 |
9 | 8i | CH2 | Cl | 19 |
10 | 8j | N-Boc | Cl | 69 |
11 | 8k | O | Cl | 27 |
12 | 8l | S | Cl | 51 |
13 | 8m | CH2 | Br | 27 |
14 | 8n | N-Boc | Br | 56 |
15 | 8o | O | Br | 66 |
16 | 8p | S | Br | 83 (44) 3 |
17 | 8q | CH2 | CH3 | 30 |
18 | 8r | N-Boc | CH3 | 57 |
19 | 8s | O | CH3 | 31 |
20 | 8t | S | CH3 | 57 |
1 Reaction conditions: 3 (0.65 mmol), 7 (0.5 mmol), HATU (0.5 mmol), EDC (0.5 mmol), Py (0.5 mmol), solvent (8 mL), N2 atmosphere, 70 °C, MW, 30 min. 2 Yields of isolated products after column chromatographic. 3 Yield using 2-MeTHF as solvent under optimized conditions.