Entry R1 Product Yieldb
1 4-Me (5a) 6a 67%
2 5-Me (5b) 6b 71%
3 6-Me (5c) 6c 69%
4 7-Me (5d) 6d 65%
5 5-OMe (5e) 6e 80%
6 4-F (5f) 6f 75%
7 5-F (5g) 6g 83%
8 6-F (5h) 6h 82%
9 7-F (5i) 6i 78%
10 5-Cl (5j) 6j 85%
11 5-Br (5k) 6k 84%
12 5-I (5l) 6l 71%
13 5-CN (5m) 6m 89%
14 5-NO2 (5n) 6n 91%
15
16
17
aReaction conditions: Pd(PhCN)2Cl2 (0.171 mol), indole (1.71 mmol), norbornene (3.41 mmol), NaHCO3 (6.84 mmol), ethyl bromoacetate (3.41 mmol), DMF with 0.5 M H2O (8 mL, total), 70°C, 14 h. bIsolated yield. cMonitored by LC-MS
Table 2: Palladium-catalyzed synthesis of various ethyl 2-(1H-indol-2-yl) acetatesa.