Water → HCID 69670126, compound

HRID 1623222Notes

Reaction equation

HRID 1623222 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][C:3]=1[OH:15].CC1C=CC(S(O[CH2:27][CH2:28][C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[O:35][CH2:34][CH2:33][C:32]3=[O:39])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C.CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[CH2:10][CH2:11][N:12]([CH2:27][CH2:28][C:29]3[CH:30]=[C:31]4[C:36](=[CH:37][CH:38]=3)[O:35][CH2:34][CH2:33][C:32]4=[O:39])[CH2:13][CH2:14]2)=[CH:4][C:3]=1[OH:15]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 59318294HCID 59318294, compoundHCID 69669886HCID 69669886, compound

Product 1

HCID 69670126HCID 69670126, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
57.5 °C

Procedure

A suspension of 2-bromo-5-(piperidin-4-ylmethyl)phenol (RE4) (500 mg, 1.9 mmol), 2-(4-oxo-3,4-dihydro-2H-chromen-6-yl)ethyl 4-methylbenzenesulfonate (RE6) (612 mg, 1.8 mmol) and potassium carbonate (489 mg, 3.5 mmol) in acetonitrile (50 mL) and dimethylformamide (20 mL) was stirred at 55-60° C. for 6 hours. The reaction mixture was cooled to room temperature, and then, water was added thereto, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained concentrated residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→chloroform:methanol=20:1) to obtain a semi-purified product of the title compound. A small amount of ethyl acetate was added thereto, and the resulting precipitate was collected by filtration, washed with ethyl acetate, and then dried under reduced pressure to obtain the title compound (5-8) of interest (37 mg, 5%) as a white powder.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe obtained concentrated residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-0d141ec031d94f89b3792c08d8cab0c5
Source dataset
uspto-grants-2014_07
Patent number
US08778970B2

Reaction notes

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