Tributylvinyltin → HCID 67417017, compound

HRID 1803496Notes

Reaction equation

HRID 1803496 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]([CH3:14])[CH3:13])=[N:7][N:6]=[CH:5]2.[CH2:15]([Sn](CCCC)(CCCC)C=C)[CH2:16]CC>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.C1(C)C=CC=CC=1>[CH3:13][N:12]([CH3:14])[C:8]1[C:9]2[C:4](=[CH:3][C:2]([CH:15]=[CH2:16])=[CH:11][CH:10]=2)[CH:5]=[N:6][N:7]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 67416416HCID 67416416, compound

Product 1

HCID 67417017HCID 67417017, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of (6-bromo-phthalazin-1-yl)-dimethyl-amine (0.32 g, 1.27 mmol) and toluene (8 mL) was purged with N2. Pd(PPh3)4 (0.4 g, 0.346 mmol) and tributyl vinyl stannane (1.11 mL, 3.80 mmol) were added and the reaction heated to 85° C. for 4 h. The reaction was cooled, filtered through celite and rinsed with CH2Cl2. The organic layers were washed with water, brine, dried (Na2SO4) and concentrated. Column chromatography (Hexanes/EtOAc) afforded the desired product (0.15 g, 59.3%) as a white solid.

Workup

  1. customwas purged with N2
  2. temperatureThe reaction was cooled
  3. filtrationfiltered through celite
  4. washrinsed with CH2Cl2
  5. washThe organic layers were washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6bee150eafde4610abc790a1fcfbf358
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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