Table 4.
Screening studies for Heck alkenylation of 5-iodo-2’-deoxyuridine with styrene under flow conditions
| |||||||||
|---|---|---|---|---|---|---|---|---|---|
| Sr.No | 1a | 5a (1.7equiv) | Styrene (1.7 equiv) | Solvent H2O: EtOH |
Flow Rate (Residence time) | Base K3PO4 (1.3 equiv) |
Pressure kPa |
Temp (°C) |
% Yield |
| 1) |
176 mg (0.083 M) |
98 ul (0.14 M) |
98 uL | 6 + 6 mL |
1 mL/min 17 m 30s) |
138 mg | 15–16 | 80 | 20 |
| 2) |
176 mg (0.083 M) |
98 ul (0.14 M) |
98 uL | 4 + 8 mL |
1 mL/min 17 m 30s) |
138 mg | 15–16 | 80 | 30 |
| 3) |
176 mg (0.067 M) |
98 ul (0.11 M) |
98 uL | 10 + 5 mL |
1 mL/min 17 m 30s) |
138 mg | 15–16 | 80 | 40 |
| 4) |
176 mg (0.067 M) |
98 ul (0.11 M) |
98 uL | 7.5 + 7.5 mL |
1 mL/min 17 m 30s) |
138 mg | 15–16 | 80 | 45 |
| 5) |
176 mg (0.067 M) |
98 ul (0.11 M) |
98 uL | 5 + 10 mL |
1 mL/min 17 m 30s) |
138 mg | 15–16 | 60 | 40 |
| 6) |
176 mg (0.067 M) |
98 ul (0.11 M) |
98 uL | 5 + 10 mL |
1 mL/min 17 m 30s) |
138 mg | 15–16 | 70 | 54 |
| 7) |
176 mg (0.067 M) |
98 ul (0.11 M) |
98 uL | 5 + 10 mL |
1 mL/min 17 m 30s) |
138 mg | 15–16 | 80 | 62 |
| 8) |
176 mg (0.067 M) |
98 ul (0.11 M) |
98 uL | 5 + 10 mL | 0.6 mL/min (29 min) | 138 mg | 8–9 | 80 | 86 |
| 9) |
176 mg (0.067 M) |
98 ul (0.11 M) |
98 uL | 5 + 10 mL | 0.5 mL/min (25 min) | 138 mg | 9–10 | 80 | 81 |
| 10) |
176 mg (0.067 M) |
98 ul (0.11 M) |
98 uL | 5 + 10 mL | 0.6 mL/min (29 min) |
90 uL (Et3N) |
8–9 | 80 | 70 |
| 11) |
176 mg (0.067 M) |
98 ul (0.11 M) |
98 uL | 5 + 10 mL | 0.6 mL/min (29 min) |
97 uL (DBU) |
8–9 | 80 | 62 |
| 12) |
176 mg (0.067 M) |
98 ul (0.11 M) |
98 uL | 5 + 10 mL | 0.6 mL/min (29 min) |
90 mg (K2CO3) |
8–9 | 80 | 65 |
| 13) |
176 mg (0.067 M) |
98 ul (0.11 M) |
98 uL | 5 + 10 mL | 0.6 mL/min (29 min) |
212 mg (Cs2CO3) |
8–9 | 80 | 74 |
| 14) |
176 mg (0.067 M) |
86 ul (1.5) (0.1 M) |
86 uL (1.5 equiv) |
5 + 10 mL | 0.6 mL/min (29 min) | 111 mg | 8–9 | 80 | 88 |
| 15) |
176 mg (0.067 M) |
75 ul (1.3) (0.087 M) |
75 uL (1.3 equiv) |
5 + 10 mL | 0.6 mL/min (29 min) | 111 mg (1.05 equiv) | 8–9 | 80 | 90 |
| 16) |
176 mg (0.067 M) |
75 ul (0.087 M) |
75 uL | 5 + 10 mL | 0.6 mL/min (29 min) |
127 mg (1.2 equiv) |
8–9 | 80 | 92 |
| 17) |
176 mg (0.067 M) |
75 ul (0.087 M) |
75 uL | 5 + 10 mL | 0.6 mL/min (29 min) | 111 mg | 8–9 | 80 | 94 |