4-Hydroxybenzyl Alcohol → [4-([1,3]Thiazolo[5,4-b]pyridin-2-yloxy)phenyl]methanol

Reaction equation

Cl[C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[CH:6][N:5]=2.[OH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[N:10]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[S:3][C:2]=1[O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][OH:11])=[CH:14][CH:15]=1

Participants

Procedure

To a solution of 2-chloro[1,3]thiazolo[5,4-b]pyridine (103 mg, 0.604 mmol) in DMF (2.0 mL) was added 4-hydroxymethyl-phenol (75 mg, 0.604 mmol, 1.0 equiv.) and Cs2CO3 (221 mg, 0.628 mmol, 1.04 equiv.). The reaction was allowed to stir at rt for 14 h. The reaction mixture was then filtered through diatomaceous earth, diluted with EtOAc (15 mL), washed with water (4×50 mL) and dried. After filtration and concentration, the desired product was obtained as a cream-colored solid (140 mg, 90%). MS (ESI): mass calcd. for C13H10N2O2S, 258.1; m/z found, 259.0 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 8.46-8.44 (m, 1H), 8.11-8.08 (m, 1H), 7.51 (dd, J=8.2, 4.7, 1H), 7.48-7.42 (m, 4H), 5.32 (t, J=5.8, 1H), 4.55 (d, J=5.8, 2H).