Methanesulfonyl chloride → Ethyl 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(methylsulfonamido)benzofuran-5-yl)benzoate

HRID 1025074Notes

Reaction equation

HRID 1025074 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[C:26]([C:27]2[CH:28]=[C:29]([CH:35]=[CH:36][CH:37]=2)[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:25][C:10]2[C:11]([C:21](=[O:24])[NH:22][CH3:23])=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[O:13][C:9]=2[CH:8]=1>N1C=CC=CC=1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[O:13][C:9]3[CH:8]=[C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[C:26]([C:27]4[CH:28]=[C:29]([CH:35]=[CH:36][CH:37]=4)[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:25][C:10]=3[C:11]=2[C:21](=[O:24])[NH:22][CH3:23])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 59275303Ethyl 3-(6-amino-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)benzoate

Product 1

HCID 59275187Ethyl 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(methylsulfonamido)benzofuran-5-yl)benzoateYield 61.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (303 μL, 3.88 mmol) was added to a stirring solution of ethyl 3-(6-amino-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)benzoate (1.40 g, 3.24 mmol) in pyridine (32 mL) at 25° C. It was allowed to stir overnight at rt. The reaction was concentrated and was purified on silica gel (Biotage, EtOAc/hexanes gradient, fraction collection at λ=254 nm) to give the titled compound (1.01 g, 61%). LC-MS retention time: 1.53 min; m/z (MH+): 511. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters XBridge 5 u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% acetonitrile/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% acetonitrile/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

Workup

  1. concentrationThe reaction was concentrated
  2. customwas purified on silica gel (Biotage, EtOAc/hexanes gradient, fraction collection at λ=254 nm)

Sources & evidence

ORD record
ord-18c250cce8c9414ba240873a26597d51
Source dataset
uspto-grants-2014_05
Patent number
US08722688B2

Reaction notes

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