Triphenylphosphine → HCID 15986279, compound

HRID 1670402Notes

Reaction equation

HRID 1670402 reaction equation
Cl[C:2]1[N:17]=[N:16][C:5]2[NH:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=1.[CH2:18]([Sn](CCCC)(CCCC)C=C)[CH2:19]CC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH:18]([C:2]1[N:17]=[N:16][C:5]2[NH:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=1)=[CH2:19]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 81998TributylvinyltinHCID 49830947HCID 49830947, compound

Product 1

HCID 15986279HCID 15986279, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-chloro-5,10-dihydro-3,4,5,10-tetraaza-dibenzo[a,d]cyclohepten-11-one from Example 2 (150 mg, 0.61 mmol) in toluene (3 ml) was added tri-n-butyl(vinyl)tin (231 mg, 0.73 mmol) followed by triphenylphosphine (4.8 mg, 0.02 mmol) and tetrakistriphenylphosphine palladium (7 mg, 0.01 mmol) and the resulting mixture was heated at 100° C. for 15 hours. The mixture was cooled to room temperature, concentrated in vacuo and purified directly by flash column chromatography (silica gel, 10% MeOH 90% dichloromethane) to afford the title compound as a yellow solid (47 mg, 33%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. custompurified directly by flash column chromatography (silica gel, 10% MeOH 90% dichloromethane)

Sources & evidence

ORD record
ord-5a0a7474e8d8429e98b6818c83e7e0c6
Source dataset
uspto-grants-2011_08
Patent number
US07994160B2

Reaction notes

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