2,6-Di-tert-butyl-4-methylphenol → HCID 21865309, compound

HRID 2056004Notes

Reaction equation

HRID 2056004 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][C:12]3[N:17]=[CH:16][N:15]=[C:14]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:19]=4OS(C(F)(F)F)(=O)=O)[CH:13]=3)[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Li+].[Cl-].[C:38](C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)[CH3:39]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:26][C:24]([F:25])([F:27])[C:21]1[CH:22]=[CH:23][C:18]([C:14]2[N:15]=[CH:16][N:17]=[C:12]([O:11][C:8]3[CH:9]=[C:10]4[C:5]([CH:4]=[CH:3][CH:2]=[N:1]4)=[CH:6][CH:7]=3)[CH:13]=2)=[C:19]([CH:38]=[CH2:39])[CH:20]=1

Participants

6

Reactant 3

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 433294Lithium ChlorideHCID 58759740HCID 58759740, compound

Product 1

HCID 21865309HCID 21865309, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of trifluoromethanesulfonic acid 2-[6-(quinolin-7-yloxy)-pyrimidin-4-yl]-5-trifluoromethyl-phenyl ester, (Example 192(a)), (600 mg, 1.2 mmol) in dioxane (6.0 mL) was added vinyltributylstannate (370 μL, 1.6 mmol, Fluka), LiCl (150 mg, 3.5 mmol, Aldrich), Pd(PPh3)4 (27 mg, 0.02 mmol, Strem) and a few crystals of 2,6-di-tert-butyl-4-methylphenol (Aldrich). The reaction mixture was stirred at reflux for 21 h. The resulting mixture was allowed to cool to room temperature and concentrated in vacuum. Purification by silica gel chromatography (1% MeOH/CH2Cl2) provided the title compound as a white amorphous solid. MS (ESI, pos. ion) m/z: 394 (M+1).

Workup

  1. temperatureat reflux for 21 h
  2. concentrationconcentrated in vacuum
  3. customPurification by silica gel chromatography (1% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-72d831ed63144a42b35c9b7c6635921d
Source dataset
uspto-grants-2008_02
Patent number
US07332511B2

Reaction notes

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