Water → N-[5-(3-nitrophenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide

HRID 18419

Reaction equation

HRID 18419 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2.[N+:18]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N+:18]([C:21]1[CH:26]=[C:25]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[CH2:7][CH:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]3)[CH:24]=[CH:23][CH:22]=1)([O-:20])=[O:19]

Participants

8

Reactant 4

HCID 962WaterHCID 16773-Nitrophenylboronic AcidHCID 10796Cesium carbonateHCID 46899809N-(5-iodo-2,3-dihydro-1H-inden-2-yl)-2-propanesulfonamide

Product 1

HCID 46900137N-[5-(3-nitrophenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamideYield 109.1%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Intermediate 2 (800 mg, 2.19 mmol) and 3-nitrophenyl boronic acid (366 mg, 2.19 mmol, Sigma Aldrich Company Ltd.) in dioxane (60 ml) was treated with cesium carbonate (1.07 g, 3.29 mmol) and water (20 ml) and degassed with argon for 2 min. Palladium (II) acetate (25 mg, 0.11 mmol) and triphenylphosphine (58 mg, 0.22 mmol) were added and the mixture was stirred at 80° C. under argon for 16 h. The reaction mixture was cooled, then partitioned between ethyl acetate (100 ml) and water (100 ml). The organic layer was separated and dried over Na2SO4 and evaporated in vacuo to give a brown oil (861 mg). This crude oil was purified using flash chromatography to give the title compound as a yellow oil (500 mg, 63%); mass spectrum: (ES−): Found 359 (MH−). C18H20N2O4S requires 360; 1H-NMR (400 MHz, CDCl3) δ 1.38 (6H, m), 2.99 (2H, m), 3.18 (1H, m), 3.38 (2H, m), 4.35 (2H, m), 7.34 (1H, d J=8 Hz), 7.45 (2H, m), 7.60 (1H, m), 7.88 (1H, dd, J=8 Hz and 1 Hz), 8.19 (1H, m), 8.41 (1H, m).

Workup

  1. customdegassed with argon for 2 min
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between ethyl acetate (100 ml) and water (100 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-1a470015f4bc4716916c32645d9d4aee
Source dataset
uspto-grants-2010_06
Patent number
US07741351B2

Linked notes

Loading…