Compound 4b
1'-tosylspiro[bicyclo[4.2.0]octa-1,3,5-triene-7,3'-indoline]
From: Remote C−H alkylation and C−C bond cleavage enabled by an in situ generated palladacycle
View in PubChem | 1H NMR | 13C NMR | MDL Molfile | ChemDraw
Compound data: CIF
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Prepared according to the general procedure outlined in the synthesis of 4a. 4b (53.6 mg, 86%) was obtained as a white solid: m.p. 150-152oC (hexane/DCM); 1H NMR (400 MHz, CDCl3) δ = 7.73 (d, J = 8.0 Hz, 1 H, Ar-H), 7.71-7.66 (m, 2 H, Ar-H), 7.30-7.22 (m, 4 H, Ar-H), 7.20-7.13 (m, 1 H, Ar-H), 7.11 (d, J = 7.2 Hz, 1 H, Ar-H), 6.97 (td, J1 = 7.5 Hz, J2 = 0.9 Hz, 1 H, Ar-H), 6.84 (dd, J1 = 7.6 Hz, J2 = 0.8 Hz, 1 H, Ar-H), 6.63 (d, J = 7.2 Hz, 1 H, Ar-H), 4.27 (d, J = 11.6 Hz, 1 H, one proton from NCH2C), 4.15 (d, J = 11.6 Hz, 1 H, one proton from NCH2C), 3.16 (d, J = 14.0 Hz, 1 H, one proton from CH2C), 3.09 (d, J = 14.0 Hz, 1 H, one proton from CH2C); 13C NMR (100 MHz, CDCl3) δ = 147.9, 144.1, 142.6, 141.7, 136.6, 134.0, 130.0, 128.6, 128.5, 127.8, 127.4, 124.4, 123.3, 123.0, 121.0, 115.3, 59.6, 54.0, 47.9, 21.5; IR (CHCl3, cm-1) 3026, 2920, 1597, 1476, 1456, 1356, 1244, 1169, 1109, 1092, 1051, 1022; HRMS (DART) calculated for C22H20NO2S [M+H+]: 362.12147, found: 362.12120.
