Potassium Carbonate → HCID 86618490, compound

HRID 1454234Notes

Reaction equation

HRID 1454234 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH:17]([CH3:19])[CH3:18])[CH2:13][CH2:12]2)=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:20][S:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOCC>[CH:17]([N:14]1[CH2:15][CH2:16][N:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:2]([O:28][C:25]3[CH:26]=[CH:27][C:22]([S:21][CH3:20])=[CH:23][CH:24]=3)=[C:3]([CH:6]=2)[CH:4]=[O:5])[CH2:12][CH2:13]1)([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 140864-(Methylthio)phenolHCID 86618489HCID 86618489, compound

Product 1

HCID 86618490HCID 86618490, compoundYield 107.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-fluoro-5-(4-isopropyl-piperazin-1-ylmethyl)-benzaldehyde (513.7 mg, 1.943 mmol), 4-methylsulfanyl-phenol (326.8 mg, 2.138 mmol), and K2CO3 (845.2 mg, 5.829 mmol) in DMF (9.0 mL) was heated at 90° C. for 3 days. After cooling to rt, the mixture was diluted with Et2O, washed with 1 N NaOH and brine, dried (Na2SO4), and concentrated. Purification by FCC followed by reverse phase chromatography gave the desired product (804.5 mg, >100%). MS (ESI): mass calcd. for C22H28N2O2S, 384.19; m/z found, 385.3 [M+H]+.

Workup

  1. temperatureAfter cooling to rt
  2. washwashed with 1 N NaOH and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by FCC

Sources & evidence

ORD record
ord-11c240e1a36d4c62ae2e1fa5f572890c
Source dataset
uspto-grants-2009_01
Patent number
US07479493B2

Reaction notes

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