HCID 21909959, compound → HCID 178443558, compound

HRID 1245272Notes

Reaction equation

HRID 1245272 reaction equation
[CH2:1]([C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]#[CH:15])[CH2:10][CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:28]=[CH:27][C:26](I)=[C:25]([F:30])[CH:24]=1>[Cu](I)I.C(NCC)C>[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:28]=[CH:27][C:26]([C:15]#[C:14][C@H:11]2[CH2:12][CH2:13][C@H:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH2:9][CH2:10]2)=[C:25]([F:30])[CH:24]=1

Participants

5

Reactant 2

HCID 21909959HCID 21909959, compoundHCID 178455745HCID 178455745, compound

Product 1

HCID 178443558HCID 178443558, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8021DiethylamineSolvent

Procedure

A mixture of 1-(trans-4-heptylcyclohexyl)acetylene (28.40 mmol), 2′,3-difluoro-4-iodobiphenyl (28.40 mmol), tetrakis(triphenylphosphine)palladium(0)dichloromethane (0.85 mmol), copper iodide (1.43 mmol), and diethylamine (200 ml) is stirred for 4 hrs at room temperature. The reaction mixture obtained is extracted with toluene (200 ml) twice. The extract is washed with water (150 ml) three times and dried over anhydrous magnesium sulfate. The toluene solution is concentrated under reduced pressure, purified by silica-gel chromatography, and further recrystallized to give the titled compound.

Workup

  1. customThe reaction mixture obtained
  2. extractionis extracted with toluene (200 ml) twice
  3. washThe extract is washed with water (150 ml) three times
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe toluene solution is concentrated under reduced pressure
  6. custompurified by silica-gel chromatography
  7. customfurther recrystallized

Sources & evidence

ORD record
ord-a118e989910e49d6a147fd18d498ef32
Source dataset
uspto-grants-2006_10
Patent number
US07125589B1

Reaction notes

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