Cesium carbonate → HCID 66786446, compound

HRID 1947468Notes

Reaction equation

HRID 1947468 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:8]=2[CH:9]=1)=[O:4].Cl[C:16]1[S:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([O:14][C:16]3[S:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)=[CH:10][C:8]=2[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 119872-ChlorobenzothiazoleHCID 12208973Methyl 5-hydroxybenzofuran-2-carboxylate

Product 1

HCID 66786446HCID 66786446, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-hydroxy-benzofuran-2-carboxylic acid methyl ester (300 mg, 1.56 mmol) in DMF (5 mL) was added 2-chlorobenzothiazole (263 mg, 1.56 mmol) and Cs2CO3 (590 mg, 1.87 mmol). The resultant suspension was warmed (50° C., 18 h). The reaction mixture was concentrated under a stream of nitrogen. The resultant residue was purified by silica gel flash chromatography using EtOAc:hexane (10-30%) to provide the title compound (406 mg, 80%). MS (ESI): mass calcd for C17H11NO4S, 325.0; m/z found, 326.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.76-7.72 (m, 2H), 7.70 (d, J=8.0, 1H), 7.67 (d, J=9.0, 1H), 7.57 (s, 1H), 7.49-7.44 (m, 1H), 7.43-7.38 (m, 1H), 7.32-7.27 (m, 1H), 4.01 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under a stream of nitrogen
  2. customThe resultant residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-2cdbb5f5041d41d4ab7814423e10d860
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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