Triethylamine → HCID 67071715, compound

HRID 1260536Notes

Reaction equation

HRID 1260536 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=2)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][CH:24]([N:27]1[C:35](=[O:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]1=[O:37])[C:25]#[CH:26].C(N(CC)CC)C>C(#N)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[N:10]=[CH:11][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:26]#[C:25][CH:24]([N:27]3[C:35](=[O:36])[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:28]3=[O:37])[CH3:23])=[CH:18][CH:17]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 6036332-(BUT-3-YN-2-YL)ISOINDOLINE-1,3-DIONEHCID 67071760HCID 67071760, compound

Product 1

HCID 67071715HCID 67071715, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

2-Benzyloxy-5-(4-bromophenoxy)pyridine (826 mg, 2.32 mmol) and 2-(1-methylprop-2-ynyl)isoindole-1,3-dione (693 mg, 3.48 mmol) were dissolved in anhydrous acetonitrile under argon and admixed with triethylamine (2.78 ml, 19.94 mmol), copper iodide (22.1 mg, 0.116 mmol) and bis(triphenylphosphine)palladium(II) chloride (81.4 mg, 0.116 mmol). The reaction mixture was stirred at 100° C. in a microwave reactor for 30 min. A further 0.75 equivalent of the reactants were added and the stirring was continued at 100° C. for a further 60 min. The batch was concentrated, admixed with ethyl acetate and water and filtered, and the organic phase was separated off and concentrated. The crude product was further reacted without purification.

Workup

  1. waitthe stirring was continued at 100° C. for a further 60 min
  2. concentrationThe batch was concentrated
  3. filtrationfiltered
  4. customthe organic phase was separated off
  5. concentrationconcentrated
  6. customThe crude product was further reacted without purification

Sources & evidence

ORD record
ord-7184be0a82f14d4da5398e16bf2ba215
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

Loading…