Iodoethane → HCID 25215196, compound

HRID 2194779Notes

Reaction equation

HRID 2194779 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:22]#[N:23])[C:5]2[CH:6]=[CH:7][N:8]([C:11]3[NH:12][C:13](=[O:21])[NH:14][C:15](=[O:20])[C:16]=3[CH:17]([CH3:19])[CH3:18])[C:9]=2[CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:30](I)[CH3:31].[C:33](OCC)(=O)C>CN(C=O)C>[CH2:30]([N:12]1[C:11]([N:8]2[C:9]3[CH:10]=[C:2]([CH3:33])[CH:3]=[C:4]([C:22]#[N:23])[C:5]=3[CH:6]=[CH:7]2)=[C:16]([CH:17]([CH3:19])[CH3:18])[C:15](=[O:20])[NH:14][C:13]1=[O:21])[CH3:31]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 67050517HCID 67050517, compound

Product 1

HCID 25215196HCID 25215196, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Chloro-1-(5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-1H-indole-4-carbonitrile (35 mg, 0.113 mmol, 1.0 eq.) was dissolved in 0.5 mL DMF. Potassium carbonate (16 mg, 1 eq.) was added and the reaction mixture was stirred at room temperature for 10 minutes. EtI (9.1 μL, 1 eq.) was added. The reaction mixture was stirred at room temperature for 2 hours. Ethyl acetate was added to the reaction mixture, followed by washing with brine. The organic layer was concentrated and purified (silica gel, 0-80% EtOAC/hexane) to give a white powder (14 mg, 37%). LC-MS shows 335.0 (M−1). 1H NMR (300 MHz, CDCl3): δ 9.37 (br, 1 H), 8.05 (s, 1H), 7.08 (m, 2H), 6.80 (d, 1H), 3.58 (m, 1H), 3.17 (m, 1H), 2.62 (s, 3H), 1.88 (m, 1H), 1.17 (dd, 6H), 1.02 (t, 3H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. washby washing with brine
  3. concentrationThe organic layer was concentrated
  4. custompurified (silica gel, 0-80% EtOAC/hexane)

Sources & evidence

ORD record
ord-4360f29a60dc49a79c6935d0665f57ce
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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