1,4-Dioxane → HCID 58097118, compound

HRID 1897964Notes

Reaction equation

HRID 1897964 reaction equation
[C:1]([N:5]1[C:9]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][C:18]3([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)[CH:14]=[C:13](OS(C(F)(F)F)(=O)=O)[CH:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[C:44]1(B(O)O)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>C(OCC)(=O)C.O>[C:1]([N:5]1[C:9]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][C:18]3([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:20][CH2:19]3)[CH:14]=[C:13]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 86649626HCID 86649626, compound

Product 1

HCID 58097118HCID 58097118, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 300 mg of 1-tert-butyl 4-ethyl 4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)-4-(((trifluoromethyl)sulfonyl)oxy)pyridin-2-yl)methyl)piperidine-1,4-dicarboxylate, 87 mg of phenylboronic acid, 69.3 mg of (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II), 201 mg of potassium phosphate, 3 ml of 1,4-dioxane and 0.3 ml of water was stirred at 100° C. overnight, followed by cooling to room temperature. The reaction mixture was diluted with ethyl acetate. An insoluble matter was filtered off using Celite, and washed with ethyl acetate. The filtrate was washed with water and brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=9/1) to give the title compound as a pale yellow solid.

Workup

  1. temperatureby cooling to room temperature
  2. filtrationAn insoluble matter was filtered off
  3. washwashed with ethyl acetate
  4. washThe filtrate was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customThe resulting residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-b41b750090b345da9a4de48fced257ba
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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