Phenyl glycidyl ether → HCID 71254084, compound

HRID 332103Notes

Reaction equation

HRID 332103 reaction equation
[Li]C.[Br:3][C:4]1[CH:5]=[C:6]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]1C=[CH:10][C:9]([C:17]#[N:18])=[CH:8][C:7]2=1.C1[C:31]2[NH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]=2[CH:22]=[C:21]([C:32]#[N:33])[CH:20]=1.[CH2:34]([O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH:35]1[O:37][CH2:36]1>C1COCC1>[Br:3][C:4]1[CH:5]=[C:6]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:36][CH:35]([OH:37])[CH2:34][O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:12]1[N:18]=[CH:17][C:9]([C:10]#[N:30])=[CH:8][C:7]2=1.[OH:37][CH:35]([CH2:34][O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:36][N:30]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]2[CH:22]=[C:21]([C:20]#[N:13])[CH:32]=[N:33][C:31]1=2

Participants

7

Reactant 4

HCID 31217Phenyl glycidyl etherHCID 21107343HCID 21107343, compoundHCID 71253927HCID 71253927, compoundHCID 178418348HCID 178418348, compound

Product 2

HCID 71254084HCID 71254084, compoundHCID 71254239HCID 71254239, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

MeLi (1.6 M in Et2O, 108 μl, 0.17 mmol) was added to a solution of the mixture of 6-bromo-9H-carbazole-3-carbonitrile and 9H-carbazole-3-carbonitrile (24.1 mg) in THF (1.0 mL) at −78° C. and stirred for 40 min. Phenyl glycidyl ether (24.1 mg, 0.16 mmol) was added at −78° C. and the reaction was stirred at 45° C. overnight. Upon completion, the solution was quenched with H2O. Ethyl acetate was added and the mixture was washed with H2O, and saturated aqueous NaCl. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. A small fraction was purified by reverse HPLC to afford the title products P7C3-S154 and P7C3-S155.

Workup

  1. stirringthe reaction was stirred at 45° C. overnight
  2. customUpon completion, the solution was quenched with H2O
  3. additionEthyl acetate was added
  4. washthe mixture was washed with H2O, and saturated aqueous NaCl
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customA small fraction was purified by reverse HPLC

Sources & evidence

ORD record
ord-7b87678618c64670b4537bf056bfb57a
Source dataset
uspto-grants-2014_11
Patent number
US08877797B2

Reaction notes

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