Potassium Phosphate, Tribasic → 4-Methanesulfonylamino-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29291Notes

Reaction equation

HRID 29291 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12](OS(C(F)(F)F)(=O)=O)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[CH3:24][S:25]([NH2:28])(=[O:27])=[O:26].C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:28][S:25]([CH3:24])(=[O:27])=[O:26])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 72879MethanesulfonamideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 865990263-Methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid ethyl ester2×

Product 1

HCID 687110224-Methanesulfonylamino-3-methyl-benzofuran-2-carboxylic acid ethyl esterYield 67%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To the product of Example 20, Step 1, 3-methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid ethyl ester (800 mg, 2.27 mmol), in 25 mL of toluene were added methane sulfonamide (650 mg, 6.82 mmol, 3 eq), Pd2 (dba)3 (208 mg, 0.23 mmol, 0.1 eq), biphenyl-2-yl-di-tert-butyl-phosphane (68 mg, 0.23 mmol, 0.1 eq), and tribasic potassium phosphate (965 mg, 4.55 mmol, 2 eq) under nitrogen and the resulting mixture was heated at reflux for 3 h. After work up and trituration, 4-methanesulfonylamino-3-methyl-benzofuran-2-carboxylic acid ethyl ester was obtained in 67% yield (450 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.3 (t, J=7.1 Hz, 3 H) 2.7 (s, 3 H) 3.1 (s, 3 H) 4.4 (q, J=7.1 Hz, 2 H) 7.3 (dd, J=7.7, 0.9 Hz, 1 H) 7.5 (dd, J=8.3, 7.6 Hz, 1 H) 7.6 (m, 1 H) 9.5 (s, 1 H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 3 h

Sources & evidence

ORD record
ord-1975c9b11e8e4d6bacdea5d65d8ae065
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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