2,6-Di-tert-butyl-4-methylphenol → HCID 23112198, compound

HRID 1373062Notes

Reaction equation

HRID 1373062 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](Br)=[CH:5][N:6]=[CH:7]2.[CH2:13](C([Sn])=C(CCCC)CCCC)[CH2:14]CC.C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C.[F-].[K+]>C1(C)C=CC=CC=1.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.C(OCC)(=O)C>[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([CH:13]=[CH2:14])=[CH:5][N:6]=[CH:7]2

Participants

8

Reactant 4

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 522689Potassium FluorideHCID 145800574-Bromoisoquinolin-5-amineHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 23112198HCID 23112198, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 5-amino-4-bromoisoquinoline obtained in Reference Example 1 (10 g), tri(n-butyl)vinyltin (21.0 ml, Tokyo Kasei Kogyo), tetrakis(triphenylphosphine)palladium(0) (1.04 g, Aldrich), and 2,6-di-tert-butyl-p-cresol (11.3 mg, Tokyo Kasei Kogyo) in toluene (90 ml) was stirred at 110° C. for 15 hours. The reaction mixture was cooled to room temperature, then added with 10% aqueous potassium fluoride (90 ml), and stirred for 4 hours. The reaction mixture was added with ethyl acetate (100 ml), and the precipitates were removed by filtration. Then, the organic layer was separated, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (7.00 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringstirred for 4 hours
  3. customthe precipitates were removed by filtration
  4. customThen, the organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-62e61fd367f547a0a45d9ee2f5f42a87
Source dataset
uspto-grants-2007_01
Patent number
US07160894B2

Reaction notes

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