Dimethylformamide → HCID 117690933, compound

HRID 1503205Notes

Reaction equation

HRID 1503205 reaction equation
I[C:2]1[N:7]=[N:6][C:5]2[O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:4]=2[CH:3]=1.[F:16][C:17]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]#[CH:28])=[CH:23][CH:22]=1)([F:19])[F:18].C(N(CC)CC)C.CN(C)C=O>[Cu](I)I.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(OCC)(=O)C>[F:16][C:17]([F:18])([F:19])[O:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]#[C:28][C:2]2[N:7]=[N:6][C:5]3[O:8][C:9]4[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=4[O:11][C:4]=3[CH:3]=2)=[CH:25][CH:26]=1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 27784941-Ethynyl-4-(trifluoromethoxy)benzeneHCID 895846403-Iodo[1,4]benzodioxino[2,3-c]pyridazine

Product 1

HCID 117690933HCID 117690933, compound

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178419050HCID 178419050, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a sealed reaction container were added 3-iodo[1,4]benzodioxino[2,3-c]pyridazine (200 mg) synthesized in Production Example 9 to be mentioned later, 4-ethynylphenyl trifluoromethyl ether (0.15 mL), copper iodide (6 mg), triethylamine (64 mg), bis(triphenylphosphine)palladium (II) dichloride (22 mg) and dimethylformamide (5 mL), and the mixture was stirred at 120° C. for 0.5 hr. Ethyl acetate and water were added, the organic layer was dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 3-{[4-(trifluoromethoxy)phenyl]ethynyl}[1,4]benzodioxino[2,3-c]pyridazine (100 mg).

Workup

  1. customTo a sealed reaction container
  2. customsynthesized in Production Example 9
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5d3a84ecd16b40b1a5150ca533ed6a41
Source dataset
uspto-grants-2015_12
Patent number
US09212147B2

Reaction notes

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