Stannane, tributyl(1-methylethenyl)- → HCID 57781108, compound

HRID 1690721Notes

Reaction equation

HRID 1690721 reaction equation
I[C:2]1[N:6]([CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[O:9][C:8]2([CH3:19])[CH3:18])[CH:5]=[N:4][CH:3]=1.[CH2:20]([Sn](CCCC)(CCCC)C(C)=C)[CH2:21][CH2:22]C>CN1C(=O)CCC1.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:21]([C:2]1[N:6]([CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[O:9][C:8]2([CH3:19])[CH3:18])[CH:5]=[N:4][CH:3]=1)([CH3:22])=[CH2:20]

Participants

5

Reactant 2

HCID 10871254Stannane, tributyl(1-methylethenyl)-HCID 57781136HCID 57781136, compound

Product 1

HCID 57781108HCID 57781108, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-(5-iodo-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one (0.700 g, 1.90 mmol) (Example 2b) in NMP (5 mL) is added tris(dibenzylideneacetone)dipalladium (0.196 g, 0.19 mmol) and trifuryl-2-yl-phospane (0.066 g, 0.285 mmol). Tributylisopropenyltin (1.25 g, 3.80 mmol) is added to the reaction mixture and it is heated to 90° C. for 24 h. The mixture is then allowed to cooled to room temperature, washed with water and extracted with ethyl acetate. The organic phase is dried over Na2SO4 and concentrated in vacuo. The residue is purified by silica gel chromatography (dichloromethane-methanol, 19:1) to give 4-(5-isopropenyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one as a white solid; (ESI) m/z 283.0 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.21 (s, 3 H), 1.50 (s, 3 H), 2.24 (br. s, 3 H), 5.31 (br. s, 1 H), 5.56 (br. s, 1 H), 5.73 (s, 1 H), 7.02 (br. s, 1 H), 7.28 (br. s, 1 H), 7.51 (d, J=7.8 Hz, 1 H), 7.69 (td, J=7.8, 1.0 Hz, 1 H), 7.81 (td, J=7.6, 1.3 Hz, 1 H), 8.25 (d, J=7.8 Hz, 1 H).

Workup

  1. temperatureto cooled to room temperature
  2. washwashed with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel chromatography (dichloromethane-methanol, 19:1)

Sources & evidence

ORD record
ord-82faf63894614ac0aa4cca703cc99c79
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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