Iodoethane → HCID 58906998, compound

HRID 1295097Notes

Reaction equation

HRID 1295097 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]2[N:18]([CH3:29])[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH:21]=2)=[CH:11][C:10]=1[CH3:30])([CH3:7])[CH3:6])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:38](I)[CH3:39]>>[CH2:1]([O:3][C:4](=[O:31])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]([C:17]2[N:18]([CH3:29])[N:19]=[C:20]([C:22]3[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=3)[CH:21]=2)[CH2:38][CH3:39])=[CH:11][C:10]=1[CH3:30])([CH3:6])[CH3:7])[CH3:2]

Participants

4

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 58907056HCID 58907056, compound

Product 1

HCID 58906998HCID 58906998, compoundYield 17%

Conditions

Temperature
95 °C

Procedure

A solution of example 15 (1.8 g, 4 mmol) in MIK (50 mL) was treated with Cs2CO3 (5 g, excess) and Ethyl iodide (2 mL). The resulting mixture was stirred at 95° C. overnight under pressure. After cooling to rt the reaction mixture was filtered off and the filtrate was evaporated off. The residue was diluted with DCM, washed with water and drying over Na2SO4 and filtration evaporation to give the title compound (320 mg, 0.68 mmol) as oil in a 17% yield after purification by flash chromatography.

Workup

  1. temperatureAfter cooling to rt the reaction mixture
  2. filtrationwas filtered off
  3. customthe filtrate was evaporated off
  4. additionThe residue was diluted with DCM
  5. washwashed with water
  6. dry with materialdrying over Na2SO4 and filtration evaporation

Sources & evidence

ORD record
ord-806113139425412e94a21bbdf45d404b
Source dataset
uspto-grants-2007_07
Patent number
US07241793B2

Reaction notes

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