Table 1. Literature Overview of Synthesis Protocols for the Erlotinib Intermediate 13.
| no. | Catalyst | Ligand, cocatalyst | Base, solvent | Conditions | X | Yield (%) | Scale (dm3) |
|---|---|---|---|---|---|---|---|
| 155 | Pd(CH3CN)2Cl2 (2 mol %) | sSPhos (6 mol %), - | TMG, HEP:H2O | 1 M, 353 K, 10 h | Br | 92 | 0.05 |
| 222 | Pd(OAc)2 (3 mol %) | P(o-tol)3 (6 mol %), - | DBU, THF | 1 M, 353 K, 6 h | Br | 86 | 0.05 |
| 356,a | 10 wt % Pd/C (2 mol %) | PPh3 (8 mol %), CuI (4 mol %) | DME:H2O, K2CO3 | 0.3 M, 353 K, 16 h | I | 78 | 0.1 |
| 468 | Pd(DPPF)Cl2 (2 mol %) | - | TMG, HEP | 0.5 M, 333 K, 3 h | Br | 99 | 0.05 |
| 552,b | PdCl2 (0.6 mol %) | PPh3 (2.4 mol %), CuCl2 (0.2 mol %) | TMG, DMF | 1 M, 348 K | Br | 73 | 0.1 |
| 653 | Pd(OAc)2 (0.3 mol %) | PPh3 (3.3 mol %), CuI (0.6 mol %) | NEt3, - | 1 M, 373 K, 7 h | Br | 75 | 2 |
| 7c | Pd1@NC (0.3 mol %) | PPh3 (1.5 mol %), CuI (6 mol %) | MeCN, NEt3 | 1 M, 353 K, 3 h | I | 49 | 2 |
a
Stability and recyclability were not assessed.
b
Reaction time not specified.
c
This work.