Tris(1,1-dimethylethyl)phosphine → HCID 178418972, compound

HRID 10558Notes

Reaction equation

HRID 10558 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([CH3:12])=[CH:5][N:6]=[CH:7]2.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[C:26]([O:30][C:31]([NH:33][C@H:34]1[CH2:39][CH2:38][C@H:37]([NH2:40])[CH2:36][CH2:35]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[C:26]([O:30][C:31]([NH:33][C@H:34]1[CH2:35][CH2:36][C@H:37]([NH:40][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[C:4]([CH3:12])=[CH:5][N:6]=[CH:7]3)[CH2:38][CH2:39]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]

Participants

8

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 219798825-Bromo-4-methylisoquinoline2×HCID 23676156Sodium t-butoxideHCID 178419079HCID 178419079, compound

Product 1

HCID 178418972HCID 178418972, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

According to the method of Example 15, Step A, the title compound was synthesized from Intermediate 93. That is, under nitrogen atmosphere, a suspension of Intermediate 93 (1.13 g), tris(dibenzylideneacetone)dipalladium(0) (0.71 g), tri(tert-butyl)phosphine (0.5 ml), trans-N-(tert-butoxycarbonyl)-1,4-cyclohexanediamine (1.04 g) and sodium tert-butoxide (0.73 g) in toluene was stirred with heating at 120° C. for 1 hour. The reaction mixture was cooled to room temperature and added with ethyl acetate (50 ml), and the insoluble matters were removed by filtration through Celite. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (456 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe insoluble matters were removed by filtration through Celite
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-7a0d394d3d824ca4a3524777a3aa12a3
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Reaction notes

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