Chloromethyl Methyl Ether → HCID 68943188, compound

HRID 576247Notes

Reaction equation

HRID 576247 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.[H-].[Na+].[CH3:32][O:33][CH2:34]Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:32][O:33][CH3:34])[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 68938945ethyl 7-bromo-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate

Product 1

HCID 68943188HCID 68943188, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice bath cooled mixture of EXAMPLE 1C (2.0 g) in THF (20 mL) was added 60% oily NaH (265 mg). The mixture was stirred for 30 minutes before adding chloromethyl methyl ether (0.54 mL). The mixture was stirred for 3 hours and overnight at room temperature, quenched by adding saturated NH4Cl mixture and extracted with diethylether. The extract was washed with water and brine and dried (Na2SO4), filtered and concentrated. The concentrate was purified with flash column chromotography on silica gel with 5% ethyl acetate/hexanes.

Workup

  1. stirringThe mixture was stirred for 3 hours and overnight at room temperature
  2. customquenched
  3. additionby adding saturated NH4Cl mixture
  4. extractionextracted with diethylether
  5. washThe extract was washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was purified with flash column chromotography on silica gel with 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-df8d02b4d5c24f5c90c9ec4550e527f2
Source dataset
uspto-grants-2015_05
Patent number
US09035047B2

Reaction notes

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