Cesium carbonate → HCID 68771084, compound

HRID 1947487Notes

Reaction equation

HRID 1947487 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([OH:14])[CH:12]=[CH:13][C:7]=2[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>CC#N>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([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:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 57353809HCID 57353809, compoundHCID 574827652-Chlorothiazolo[4,5-b]pyridine hydrochloride

Product 1

HCID 68771084HCID 68771084, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-hydroxy-benzo[b]thiophene-2-carboxylic acid methyl ester (0.18 g, 0.9 mmol) in MeCN (9 mL) was added Cs2CO3 (0.6 g, 1.8 mmol), 2-chloro-thiazolo[4,5-b]pyridine hydrochloride (0.18 g, 0.9 mmol) and the reaction mixture was stirred (rt, 3 h). The reaction mixture was filtered and concentrated in vacuum to provide the title compound as pink solid (0.18 g, 60%). MS (ESI): mass calcd. for C11H10N2O3S2, 342.0; m/z found, 343.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.58 (dd, J=4.8, 1.6, 1H), 8.12-8.00 (m, 3H), 7.92 (d, J=8.8, 1H), 7.46 (dd, J=8.8, 2.2, 1H), 7.24-7.18 (m, 1H), 3.96 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-17635427798347d08f712bff342898a3
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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