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

HRID 857688Notes

Reaction equation

HRID 857688 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-3fd544a951164c1bb45bfbc377e3732f
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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