Potassium Carbonate → 3-[{4-[(4-Acetyl-3-hydroxy-2-methyl-phenylamino)-methyl]-phenyl}-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile

HRID 1161040Notes

Reaction equation

HRID 1161040 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([OH:11])[C:3]=1[CH3:12].I[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[C:25]#[N:26])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([CH:21]([O:30][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=3)[C:25]#[N:26])=[CH:19][CH:20]=2)=[C:3]([CH3:12])[C:4]=1[OH:11])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57438306HCID 57438306, compoundHCID 574383081-(4-Amino-2-hydroxy-3-methyl-phenyl)-ethanone

Product 1

HCID 666995503-[{4-[(4-Acetyl-3-hydroxy-2-methyl-phenylamino)-methyl]-phenyl}-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrileYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(4-amino-2-hydroxy-3-methyl-phenyl)-ethanone (300 mg, 1.8 mmol) and 3-[(4-Iodomethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile (865 mg, 2.0 mmol)) in anhydrous DMF (1.5 mL) under Ar gas at RT is added K2CO3 (303 mg, 2.2 mmol). The reaction mixture is heated at 50° C. overnight. The reaction mixture is quenched into water and extracted with EtOAc (3×). The organic layers are combined, washed with brine, dried over Na2SO4 and concentrated. The residue is purified by flash chromatography using 25% EtOAc/hexane as eluent. Obtained is the title compound as a yellow foam (538 mg, 64%). LC-MS (m/e): 469 (M−1).

Workup

  1. customThe reaction mixture is quenched into water
  2. extractionextracted with EtOAc (3×)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography
  7. customObtained

Sources & evidence

ORD record
ord-9cccf387e8c2404685b9f4facb86c73e
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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