Acetonitrile → HCID 11305148, compound

HRID 2218038Notes

Reaction equation

HRID 2218038 reaction equation
C(#N)C.Br[C:5]1[CH:6]=[C:7]([C:11]2[C:12]3[CH:23]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:21]([O:30][CH3:31])=[CH:20][C:13]=3[N:14]([CH3:19])[C:15](=[O:18])[CH2:16][N:17]=2)[CH:8]=[CH:9][CH:10]=1.[C:32]1(C#C)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cu](I)I.Cl[Pd]Cl.C(N(CC)CC)C>[C:37]([C:5]1[CH:6]=[C:7]([C:11]2[C:12]3[CH:23]=[C:22]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:21]([O:30][CH3:31])=[CH:20][C:13]=3[N:14]([CH3:19])[C:15](=[O:18])[CH2:16][N:17]=2)[CH:8]=[CH:9][CH:10]=1)#[C:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 11487361HCID 11487361, compound

Product 1

HCID 11305148HCID 11305148, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 83717Copper iodideCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

To 10 mL of degazed acetonitrile, 5-(3-bromo-phenyl)-8-methoxy-1-methyl-7-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one Example 62 (200 mg, 0.46 mmol), phenylacetylene (715 μL, 2.30 mmol), copper iodide (15 mg, 0.08 mmol), triphenylphosphine (30 mg, 0.11 mmol), PdCl2 (10 mg, 0.06 mmol) and triethylamine (0.9 mL) were added. The mixture was stirred for 16 hours at 50° C. under nitrogen atmosphere. The working solution was evaporated under vacuum. The residue was partitioned from water and ethyl acetate and extracted two more times with ethyl acetate. The organic phase was dried over Na2SO4 and concentrated until dryness. The residue was purified by chromatography (eluant: Hexane/EtOAc: 1/1). The title compound was crystallised from ether/pentane to afford 134 mg of the title compound: beige solid, yield=90%.

Workup

  1. customThe working solution was evaporated under vacuum
  2. customThe residue was partitioned from water and ethyl acetate
  3. extractionextracted two more times with ethyl acetate
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated until dryness
  6. customThe residue was purified by chromatography (eluant: Hexane/EtOAc: 1/1)
  7. customThe title compound was crystallised from ether/pentane

Sources & evidence

ORD record
ord-92d0e65497324b458d608db6ca991bad
Source dataset
uspto-grants-2008_08
Patent number
US07410963B2

Reaction notes

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