Phenyl glycidyl ether → HCID 71253769, compound

HRID 1752224Notes

Reaction equation

HRID 1752224 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[CH:11]=[N:12][C:13]([C:15]#[N:16])=[CH:14][C:5]2=1.C[Li].[O:19]1[CH:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:20]1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:20][CH:21]([OH:19])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:6]1[CH:11]=[N:12][C:13]([C:15]#[N:16])=[CH:14][C:5]2=1

Participants

4

Reactant 3

HCID 31217Phenyl glycidyl etherHCID 71254133HCID 71254133, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 71253769HCID 71253769, compoundYield 90%

Conditions

Temperature
-78 °C

Procedure

6-bromo-9H-pyrido[3,4-b]indole-3-carbonitrile (21.3 mg, 0.785 mmol) was added to a flask and purged with nitrogen. THF was added and the solution was cooled to −78° C. Methyl lithium (1.6 M in Et2O) (1.1 eq) was added and was stirred for 30 minutes. 1,2-epoxy-3-phenoxypropane (0.011 mL, 0.824 mmol) was added with gradual warming to 45° C. Upon completion the reaction was quenched with 1 N HCl and extracted 3× with EtOAc. The organic layer was washed with H2O, brine, and dried over Na2SO4. The crude mixture was purified on SiO2 (0 to 50% EtOAc/hexanes to afford the desired product in 90% yield.

Workup

  1. custompurged with nitrogen
  2. additionTHF was added
  3. temperaturewith gradual warming to 45° C
  4. customUpon completion the reaction was quenched with 1 N HCl
  5. extractionextracted 3× with EtOAc
  6. washThe organic layer was washed with H2O, brine
  7. dry with materialdried over Na2SO4
  8. customThe crude mixture was purified on SiO2 (0 to 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-f0aff18a2cf74195953aaa16953a085a
Source dataset
uspto-grants-2015_10
Patent number
US09162980B2

Reaction notes

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