2-Bromoethyl methyl ether → HCID 67046182, compound

HRID 606009Notes

Reaction equation

HRID 606009 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[N:12]=[C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[C:21]([CH2:25][OH:26])[CH:22]=[CH:23][CH:24]=3)=[CH:15][N:14]2[CH:27]=1.[CH3:28][O:29][CH2:30][CH2:31]Br.[F-].[K+]>CO.CN(C)C=O>[CH3:28][O:29][CH2:30][CH2:31][O:26][CH2:25][C:21]1[CH:20]=[C:19]([C:16]2[CH:17]=[CH:18][C:13]3[N:14]([CH:27]=[C:11]([C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH:1]=4)[N:12]=3)[CH:15]=2)[CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 809722-Bromoethyl methyl etherHCID 522689Potassium FluorideHCID 24856032HCID 24856032, compound

Product 1

HCID 67046182HCID 67046182, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 21901440N,N-dimethylformamide methanolSolvent

Conditions

Temperature
80 °C

Procedure

100 mg of [3-(2-naphthalen-2-ylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol (Example 2) and 120 mg of 2-bromoethanol methyl ether are dissolved in 5 ml of a 1/1 methanol/dimethylformamide mixture, in a pressure tube, and 1 g of potassium fluoride on alumina is added thereto. The tube is closed and heated for 16 h at 80° C. After cooling, the mineral is removed by filtration and washed with dichloromethane. The filtrate is concentrated under reduced pressure and purified by silica gel chromatography, elution being carried out with a 99/1 dichloromethane/methanol mixture. An oil which crystallizes from 5 ml of diisopropyl ether is obtained. The precipitate is recovered by filtration, washed with diisopropyl ether and dried under reduced pressure. 44 mg of compound are obtained. Mp=80-82° C. 1H NMR (DMSO-d6, δ in ppm): 3.25 (m, 3H) 3.55 (m, 4H); 4.57 (s, 2H); from 7.27 to 7.80 (m, 8H); from 7.82 to 8.16 (m, 4H); 8.52 (m, 2H); 8.89 (m, 1H). M+H=409.

Workup

  1. customThe tube is closed
  2. temperatureAfter cooling
  3. customthe mineral is removed by filtration
  4. washwashed with dichloromethane
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. custompurified by silica gel chromatography, elution
  7. customAn oil which crystallizes from 5 ml of diisopropyl ether
  8. customis obtained
  9. filtrationThe precipitate is recovered by filtration
  10. washwashed with diisopropyl ether
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-02837d3662a24886814521d7d680f877
Source dataset
uspto-grants-2011_03
Patent number
US07915284B2

Reaction notes

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