Table 2.
Flow catalytic Suzuki-Miyaura cross-coupling of 5-iodo-2’-deoxycytidine with 3-methoxyphenyl boronic acid
| ||||||||
|---|---|---|---|---|---|---|---|---|
| Sr.No | 1b | 2a (1.3 eq) |
Catalyst mol% |
Solvent H2O: EtOH |
Flow Rate (Residence time) | Pressure (kPa) |
Base 1.05 eq |
%Yield |
| 1) |
177 mg (0.083 M) |
98 mg (0.107 M) |
1 | 8 + 4 ml |
0.7 mL/min (25 min) |
9–10 | 111 mg | 20 |
| 2) |
177 mg (0.063 M) |
98 mg (0.081 M) |
1 | 10 + 6 ml |
0.7 mL/min (25 min) |
9–10 | 111 mg | 38 |
| 3) |
177 mg (0.063 M) |
98 mg (0.081 M) |
1 | 10 + 6 ml |
0.6 mL/min (29 min) |
8–9 | 111 mg | 69 |
| 4) |
177 mg (0.050 M) |
98 mg (0.064 M) |
1 | 12 + 8 ml |
0.7 mL/min (25 min) |
9–10 | 111 mg | 74 |
| 5) |
177 mg (0.050 M) |
98 mg (0.064 M) |
1 | 12 + 8 ml |
0.6 mL/min (29 min) |
8–9 | 111 mg | 90 |
| 6) |
177 mg (0.050 M) |
98 mg (0.064 M) |
1 | 12 + 8 ml |
0.5 mL/min (35 min) |
6–7 | 111 mg | 90 |
| 7) |
177 mg (0.050 M) |
98 mg (0.064 M) |
0.75 | 12 + 8 ml |
0.5 mL/min (35 min) |
6–7 | 111 mg | 59 |
| 8) |
177 mg (0.050 M) |
98 mg (0.064 M) |
0.5 | 12 + 8 ml |
0.5 mL/min (35 min) |
6–7 | 111 mg | 43 |