Hydrochloric Acid → HCID 66852213, compound

HRID 1631199Notes

Reaction equation

HRID 1631199 reaction equation
C(N([CH2:6][CH3:7])CC)C.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([CH3:19])[CH3:18])=[CH:12][CH:11]=1)#[CH:9].Cl.CN(C)[CH:23]=[O:24]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:16]([C:13]1[CH:14]=[CH:15][C:10]([C:8]#[C:9][C:9]2[CH:8]=[C:10]3[C:15](=[CH:6][CH:7]=2)[C:23](=[O:24])[CH2:13][CH2:12][CH2:11]3)=[CH:11][CH:12]=1)[CH:17]([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 50540331-Ethynyl-4-(2-methylpropyl)benzene

Product 1

HCID 66852213HCID 66852213, compound

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

To cuprous iodide (48 mg), a solution of the compound (353 mg) prepared in Reference Example 06 in N,N-dimethylformamide (3 mL), triethylamine (279 μl) and a solution of 1-ethynyl-4-isobutylbenzene (158 mg) in N,N-dimethylformamide (5 mL) were added, followed by stirring at room temperature for 5 minutes. Next, tetrakis(triphenylphosphine) palladium (0) (58 mg) was added thereto, followed by stirring for 19 hours. After adding 1 N hydrochloric acid, the mixture was extracted with ethyl acetate. The organic layer was successively washed with 1 N hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried and concentrated. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=95:5) to thereby give the title compound (209 mg) having the following physical properties.

Workup

  1. stirringby stirring for 19 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was successively washed with 1 N hydrochloric acid
  4. dry with materiala saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried
  5. concentrationconcentrated
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-542c94496b554032bab442ae4258120e
Source dataset
uspto-grants-2014_07
Patent number
US08791159B2

Reaction notes

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