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

HRID 1807451Notes

Reaction equation

HRID 1807451 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

5

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 10796Cesium carbonateHCID 133428032-Chloro-[1,3]thiazolo[5,4-b]pyridine

Product 1

HCID 57448386[4-([1,3]Thiazolo[5,4-b]pyridin-2-yloxy)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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).

Workup

  1. filtrationThe reaction mixture was then filtered through diatomaceous earth
  2. additiondiluted with EtOAc (15 mL)
  3. washwashed with water (4×50 mL)
  4. customdried
  5. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-c9b44cb1c137489e9e79acd7eb294aac
Source dataset
uspto-grants-2013_01
Patent number
US08357684B2

Reaction notes

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