Sodium Carbonate → (S)-methyl 3-((2-(1-methylethylsulfonamido)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)benzoate

HRID 473076Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@H:7]([NH:12][S:13]([CH:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])[CH2:6]2.CC1(C)COB([C:26]2[CH:27]=[C:28]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=2)[C:29]([O:31][CH3:32])=[O:30])OC1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C(Cl)Cl>[CH3:17][CH:16]([S:13]([NH:12][C@@H:7]1[CH2:6][C:5]2[C:9](=[CH:10][CH:11]=[C:3]([CH2:2][C:26]3[CH:27]=[C:28]([CH:33]=[C:34]([C:36]([F:37])([F:39])[F:38])[CH:35]=3)[C:29]([O:31][CH3:32])=[O:30])[CH:4]=2)[CH2:8]1)(=[O:15])=[O:14])[CH3:18]

Participants

Conditions

Temperature: 100 °C

Procedure

To (S)-N-(5-(chloromethyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide (0.160 mmol, 46 mg) in THF (1 mL) was added methyl 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5-(trifluoromethyl)benzoate (0.160 mmol, 50.5 mg), Bromo(N-succinimidyl)bis-(triphenylphosphine)palladium(II) (7.99 μmol, 6.46 mg) and sodium carbonate (1.000 mmol, 0.5 mL). The reaction was heated to 100° C. for 10 minutes by microwave irradiation before diluting with DCM and filtering through a hydrophobic frit. The solvent was removed in vacuo before redissolving in MeCN (500 μL) and purifying by reverse phase preparative chromatography to give (S)-methyl 3-((2-(1-methylethylsulfonamido)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)benzoate (23.2 mg, 31.9%). MS (ESI): m/z [M+H]+ 456.0

Workup

filtrationfiltering through a hydrophobic frit
customThe solvent was removed in vacuo
dissolutionbefore redissolving in MeCN (500 μL)
custompurifying by reverse phase preparative chromatography

Sources & evidence

ORD record: ord-fc2942bd7d70412598fe42487aad2c73
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633237B2

Reaction notes

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