1,2-Dibromoethane → HCID 58081151, compound

HRID 2364948Notes

Reaction equation

HRID 2364948 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[C:6]([OH:8])[CH:7]=1.Br[CH2:17][CH2:18]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]([CH:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[CH2:17][CH2:18][O:8][C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 66726147HCID 66726147, compound

Product 1

HCID 58081151HCID 58081151, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of intermediate D9 (0.433 g, 1.591 mmol), 1,2-dibromoethane (0.411 ml, 4.773 mmol and potassium carbonate (1.099 g, 7.955 mmol) in DMF (10 ml) was heated at 180° C. for 15 min. under microwave irradiation. After cooling to r.t. the r.m. was filtered through diatomaceous earth. The filtrate was evaporated in vacuo. The crude residue was purified by column chromatography (silica gel; DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield a colorless oil that crystallized to yield D11 (0.267 g, 56%) as a white solid.

Workup

  1. temperatureAfter cooling to r.t. the r.m
  2. filtrationwas filtered through diatomaceous earth
  3. customThe filtrate was evaporated in vacuo
  4. customThe crude residue was purified by column chromatography (silica gel; DCM as eluent)
  5. customThe desired fractions were collected
  6. customevaporated in vacuo
  7. customto yield a colorless oil that
  8. customcrystallized

Sources & evidence

ORD record
ord-75e1539736e64d28b5f72714542694b1
Source dataset
uspto-grants-2014_04
Patent number
US08697689B2

Reaction notes

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