Water → 6-(Thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-2-carboxylic acid ethyl ester

HRID 1947472Notes

Reaction equation

HRID 1947472 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Cl.Cl[C:24]1[S:25][C:26]2[C:27]([N:32]=1)=[N:28][CH:29]=[CH:30][CH:31]=2.O>CC#N>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[C:13]([O:15][C:24]3[S:25][C:26]4[C:27]([N:32]=3)=[N:28][CH:29]=[CH:30][CH:31]=4)[CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 574827652-Chlorothiazolo[4,5-b]pyridine hydrochlorideHCID 66786469Ethyl 6-hydroxybenzofuran-2-carboxylate

Product 1

HCID 687707006-(Thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-2-carboxylic acid ethyl esterYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-hydroxy-benzofuran-2-carboxylic acid ethyl ester (2.0 g, 10 mmol) in MeCN (100 mL) added Cs2CO3 (6.3 g, 19 mmol) followed by 2-chloro-thiazolo[4,5-b]pyridine hydrochloride (2.0 g, 10 mmol) and the reaction mixture was stirred (rt, 12 h). The reaction mixture was treated with H2O (50 mL) and the solid was filtered to afford the title compound as a beige solid (2.3 g, 69%). MS (ESI): mass calcd. for C17H12N2O4S, 340.1; m/z found, 341.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.58 (dd, J=4.8, 1.6, 1H), 8.04 (dd, J=7.9, 1.6, 1H), 7.75-7.69 (m, 2H), 7.55 (d, J=0.8, 1H), 7.42 (dd, J=8.6, 2.1, 1H), 7.22 (dd, J=7.9, 4.8, 1H), 4.46 (q, J=7.1, 2H), 1.44 (t, J=7.1, 3H).

Workup

  1. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-2a80eae4d8c049cbbe8f27f9f8df8c41
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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