Dimethylformamide → HCID 69561981, compound

HRID 2299000Notes

Reaction equation

HRID 2299000 reaction equation
[Li+].[Cl-].C([Sn](CCCC)(CCCC)[CH:8]=[CH:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:20]#[N:21])[CH:14]=[CH:13]2)CCC.[CH3:30][N:31]([CH:33]=O)C>C(OCC)(=O)C.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>[CH:14]([C:30]1[C:11]2[C:10](=[CH:19][CH:18]=[C:17]([CH:8]=[CH:9][C:10]3[CH:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[CH:16]=[C:15]([C:20]#[N:21])[CH:14]=[CH:13]4)[CH:12]=2)[CH2:9][CH2:33][N:31]=1)([CH3:15])[CH3:13]

Participants

6

Reactant 3

HCID 6228Dimethylformamide2×HCID 433294Lithium ChlorideHCID 69560666HCID 69560666, compound

Product 1

HCID 69561981HCID 69561981, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of Example 13I (70 mg, 0.23 mmol), dichlorobis(triphenylphosphine)palladium (II) (7.0 mg, 0.01 mmol), and LiCl (31 mg, 0.73 mmol) in DMF (1.7 mL) was treated dropwise with a solution of Example 13E (120 mg, 0.26 mmol) in DMF (0.2 mL). The mixture was heated to 80° C., stirred for 1.75 hours, cooled to room temperature, diluted with ethyl acetate, washed with H2O and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes to provide the desired product.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with H2O and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6699ac0572de40a29d93531938b80132
Source dataset
uspto-grants-2002_12
Patent number
US06495562B1

Reaction notes

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