Isopropyl iodide → HCID 87227706, compound

HRID 557489Notes

Reaction equation

HRID 557489 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[CH2:21][C:20]([CH3:23])=[CH:19]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH:30](I)([CH3:32])[CH3:31]>CN(C=O)C>[CH:30]([N:11]([CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][CH2:17][C:18]2[C:22]=1[CH:21]=[C:20]([CH3:23])[CH:19]=2)[S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)(=[O:10])=[O:9])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 58418752HCID 58418752, compound

Product 1

HCID 87227706HCID 87227706, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

At room temperature, to a solution of 11.4 g (34.8 mmol) of 4-methyl-N-[2-(2-methyl-1H-inden-7-yl)ethyl]-benzenesulfonamide in 75 mL of dry DMF, 17.0 g (52.3 mmol) of Cs2CO3 was added, and then 11.9 g (69.8 mmol) of iPrI was added dropwise over a period of 10 minutes. This mixture was then stirred for 3 days at 50° C., and then evaporated via vacuum. To the residue, 200 mL of water and 200 mL of dichloromethane were added. The organic layer was separated, and the aqueous layer was washed with 200 mL of dichloromethane. The combined organic extract was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent—dichloromethane). Yield, 10.9 g (85%) of white solid. This product was further used without additional purification. 1H NMR (CDCl3): δ 7.20 (m, 1H, 5-H in indenyl), 7.15 (m, 1H, 6-H in indenyl), 6.95 (m, 1H, 4-H in indenyl), 6.52 (m, 1H, 3-H in indenyl), 4.06 (set, J=6.8 Hz, 1H, CHMe2), 3.13-3.27 (m, 4H, 1,1′-H in indenyl and CH2CH2N), 2.96-3.07 (m, 2H, CH2CH2N), 2.34 (s, 3H, 2-Me in indenyl), 0.99 (d, J=6.8 Hz, 6H, CHMe2). Anal. Calc. for C22H27NO2S: C, 71.51; H, 7.36; N, 3.79%. Found: C, 72.01; H, 7.49; N, 3.33%.

Workup

  1. customevaporated via vacuum
  2. additionTo the residue, 200 mL of water and 200 mL of dichloromethane were added
  3. customThe organic layer was separated
  4. washthe aqueous layer was washed with 200 mL of dichloromethane
  5. extractionThe combined organic extract
  6. customwas evaporated to dryness
  7. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent—dichloromethane)
  8. customYield
  9. customThis product was further used without additional purification

Sources & evidence

ORD record
ord-28481a713b954bde9c5255e576ab0248
Source dataset
uspto-grants-2011_11
Patent number
US08058461B2

Reaction notes

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