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

HRID 1807449Notes

Reaction equation

Cl.Cl[C:3]1[S:4][C:5]2[C:6]([N:11]=1)=[N:7][CH:8]=[CH:9][CH:10]=2.C([O-])([O-])=O.[K+].[K+].[OH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1>CC#N>[S:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:11]=[C:3]1[O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][OH:18])=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 2-chloro[1,3]thiazolo[4,5-b]pyridine hydrochloride (1.0 equiv.) in CH3CN (0.25 M), was added K2CO3 (powder, 325 mesh; 2.1 equiv.). The mixture was stirred at 50° C. under N2 for 3 h prior to the addition of 4-hydroxymethyl-phenol (1.0 equiv.). The reaction mixture was heated at reflux for 3 h and cooled to rt. Some product precipitated out from the reaction solution and was dissolved by adding CH2Cl2. The insoluble inorganic salt was then filtered off and washed with CH2Cl2. The filtrate solution was concentrated to give the title compound (99%), which was used without further purification. MS (ESI): mass calcd. for C13H10N2O2S, 258.1; m/z found, 258.9 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.56 (ddd, J=4.9, 1.7, 0.4, 1H), 8.02 (ddd, J=7.9, 1.7, 0.4, 1H), 7.48-7.38 (m, 4H), 7.21 (ddd, J=7.9, 4.8, 0.4, 1H), 4.74 (s, 2H).

Workup

temperatureThe reaction mixture was heated
temperatureat reflux for 3 h
temperaturecooled to rt
customSome product precipitated out from the reaction solution
dissolutionwas dissolved
additionby adding CH2Cl2
filtrationThe insoluble inorganic salt was then filtered off
washwashed with CH2Cl2
concentrationThe filtrate solution was concentrated

Sources & evidence

ORD record: ord-426441979cb14d25af0788a37a7a3442
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357684B2

Reaction notes

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