Water → HCID 68768645, compound

HRID 1947492Notes

Reaction equation

HRID 1947492 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[O:7][CH:6]=1)=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].Cl.Cl[C:23]1[S:24][C:25]2[C:26]([N:31]=1)=[N:27][CH:28]=[CH:29][CH:30]=2.O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C:23]3[S:24][C:25]4[C:26]([N:31]=3)=[N:27][CH:28]=[CH:29][CH:30]=4)=[CH:13][C:8]=2[O:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 574827652-Chlorothiazolo[4,5-b]pyridine hydrochlorideHCID 59577559Methyl 6-hydroxybenzofuran-3-carboxylate

Product 1

HCID 68768645HCID 68768645, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-hydroxy-benzofuran-3-carboxylic acid methyl ester (1.7 g, 8.8 mmol) in DMF (88 mL) was added Cs2CO3 (8.6 g, 1.8 mmol) followed by 2-chloro-thiazolo[4,5-b]pyridine hydrochloride (1.8 g, 8.8 mmol) and the reaction mixture was stirred (rt, 3 h). The reaction mixture was treated with water (50 mL) to form a solid. The solid was filtered to provide the title compound as a white solid (2.5 g, 87%). MS (ESI): mass calcd. for C16H10N2O4S, 326.0; m/z found, 327.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.57 (dd, J=4.8, 1.6, 1H), 8.30 (s, 1H), 8.11 (d, J=8.6, 1H), 8.03 (dd, J=7.9, 1.6, 1H), 7.75 (d, J=2.1, 1H), 7.41 (dd, J=8.6, 2.1, 1H), 7.22 (dd, J=7.9, 4.8, 1H), 3.97 (s, 3H).

Workup

  1. customto form a solid
  2. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-6cf5fefdded046fea5e8669b55415b1e
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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