Phenol → HCID 45254924, compound

HRID 1887474Notes

Reaction equation

HRID 1887474 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].Br[C:10]1[N:15]2[C:16]([NH:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[N:18]=[C:14]2[CH:13]=[CH:12][CH:11]=1.[O-]C1C=CC=CC=1.[Na+]>CN(C=O)C>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:17]1[N:18]=[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([O:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:15]2[C:16]=1[NH:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 996PhenolHCID 4445035Phenolate SodiumHCID 5360545SodiumHCID 45254538HCID 45254538, compound

Product 1

HCID 45254924HCID 45254924, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Phenol (40.43 mg, 0.687 mmol) was dissolved in DMF (5 ml) and sodium metal (10.31 mg, 0.687 mmol) was added portion-wise. 5-Bromo-2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine 42 (139.1 mg, 0.344 mmol) was added to this sodium phenoxide solution and heated at 90° C. for 4 h. The reaction was quenched with water and extracted into ethyl acetate. The product was purified by column chromatography, elution ethyl acetate:hexane.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted into ethyl acetate
  3. customThe product was purified by column chromatography, elution ethyl acetate

Sources & evidence

ORD record
ord-6495e51c910445eb92a5cedca44f2e1f
Source dataset
uspto-grants-2013_08
Patent number
US08501767B2

Reaction notes

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