Isopropyl iodide → HCID 91523227, compound

HRID 857367Notes

Reaction equation

HRID 857367 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH:5]1[C:9]2=[CH:10][C:11]3[C:12]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:13][C:14]([OH:17])=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1.I[CH:24]([CH3:26])[CH3:25].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH:5]1[C:9]2=[CH:10][C:11]3[C:12]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:13][C:14]([O:17][CH:24]([CH3:26])[CH3:25])=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 58760708HCID 58760708, compound

Product 1

HCID 91523227HCID 91523227, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To methyl [6-hydroxy-8-(methylsulfonyl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl]acetate (Example 23, Step 2, 130 mg, 0.4 mmol) in DMF (1.5 mL) at r.t. was added 2-iodopropane (300 μL, 3 mmol) and Cs2CO3 (300 mg, 0.92 mmol). The reaction mixture was stirred for 15 minutes, and was then quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were dried over NaSO4 and concentrated. The residue was purified by silica gel chromatography to give the title compound (100 mg).

Workup

  1. customwas then quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over NaSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8b04061330d441a9b87d46db6660426d
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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