Cesium carbonate → HCID 21084058, compound

Reaction equation

Br[CH2:2][CH2:3][OH:4].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]3[C:19]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[S:21][C:13]2=3)=[CH:8][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[OH:4][CH2:3][CH2:2][O:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]3[C:19]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[S:21][C:13]2=3)=[CH:10][CH:11]=1

Participants

Procedure

2-Bromoethanol (0.148 mL, 2.08 mmol) was added to the compound of Example 89 (370 mg, 0.95 mmol) and Cs2CO3 (342 mg, 1.04 mmol) in DMF (5 mL) and the mixture heated at 80° for 2 days. The solvent was removed in vacuo and the residue partitioned between EtOAc and HCl (10%). The aqueous phase was extracted with EtOAc (2×20 mL). The combined organics were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography on silica (2% to 10% MeOH in DCM) to give the title compound (73 mg, 18%). δH (CDCl3) 7.44–7.28 (8H, m), 7.07 (2H, d, J 8 Hz), 6.52 (1H, d, J 9.6 Hz), 4.12–3.93 (6H, m), 1.06 (3H, t, J 7.1 Hz). LCMS (ES+) RT 3.42 minutes, 436 (M+H)+.