Dichloromethane → HCID 86683445, compound

HRID 2174954Notes

Reaction equation

HRID 2174954 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:29])[C:13](=[N:26][C:27]#[N:28])[N:14]([C:15]4[CH:16]=[N:17][C:18]([C:21]([C:24]#[N:25])([CH3:23])[CH3:22])=[CH:19][CH:20]=4)[C:5]=3[C:4]=2[CH:3]=1.[B:30]1(B2OC(C)(C)C(C)(C)O2)[O:34]C(C)(C)C(C)(C)[O:31]1.C([O-])(=O)C.[K+].C(Cl)Cl>O1CCOCC1.C(OCC)(=O)C>[C:27]([N:26]=[C:13]1[N:12]([CH3:29])[C:6]2[CH:7]=[N:8][C:9]3[CH:10]=[CH:11][C:2]([B:30]([OH:34])[OH:31])=[CH:3][C:4]=3[C:5]=2[N:14]1[C:15]1[CH:16]=[N:17][C:18]([C:21]([C:24]#[N:25])([CH3:23])[CH3:22])=[CH:19][CH:20]=1)#[N:28]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 87097715HCID 87097715, compound

Product 1

HCID 86683445HCID 86683445, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

N-(8-bromo-1-(6-(2-cyanopropan-2-yl)pyridin-3-yl)-3-methyl-1H-imidazo[4,5-c]quinolin-2(3H)-ylidene)cyanamide (2.463 mmol) was dissolved in 15 mL of dioxane under argon atmosphere. Bis(pinacolato)diboron (1.347 mmol), potassium acetate (2.246 mmol) and (1,1-bis(diphenylphosphino)ferrocene)-dichloropalladium (II) complex with DCM (50 mg) while stirring. The reaction mixture was refluxed for 8 h. After completion of the reaction, the reaction mixture was cooled and diluted with 15 mL ethyl acetate and filtered through celite. The filtrate was concentrated and the crude product was purified (silica gel column, ethyl acetate/petroleum ether as eluent) to obtain the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 8 h
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture was cooled
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated
  6. customthe crude product was purified (silica gel column, ethyl acetate/petroleum ether as eluent)

Sources & evidence

ORD record
ord-b7eff81491274d668f3545ffa128cdf9
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

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