1-Propanol → HCID 66872868, compound

HRID 1967522Notes

Reaction equation

HRID 1967522 reaction equation
[CH:1]([B-](F)(F)F)=[CH2:2].[K+].C(N(CC)CC)C.C(O)CC.Br[C:20]1[CH:21]=[C:22]([O:44][CH3:45])[C:23]([NH:26][C:27](=[O:43])[C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([S:34]([N:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)(=[O:36])=[O:35])[CH:29]=2)=[N:24][CH:25]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(OCC)(=O)C>[CH3:45][O:44][C:22]1[C:23]([NH:26][C:27](=[O:43])[C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([S:34]([N:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)(=[O:36])=[O:35])[CH:29]=2)=[N:24][CH:25]=[C:20]([CH:1]=[CH2:2])[CH:21]=1

Participants

7

Reactant 4

HCID 10311-PropanolHCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 66872716HCID 66872716, compound

Product 1

HCID 66872868HCID 66872868, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

At room temperature, [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (9.7 mg), potassium vinyltrifluoroborate (10.6 mg) and triethylamine (0.010 mL) were added in that order to an n-propanol (1.0 mL) solution of the compound (30.0 mg) obtained in Example 106, and stirred at 80° C. for 10 hours. After left cooled, ethyl acetate was added to the reaction liquid, then washed three times with water, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was purified through silica gel column chromatography (NH Biotage Column, ethyl acetate/hexane=from 0% to 80%, gradient) to give the entitled compound (11.0 mg, 42%) as a colorless oily substance.

Workup

  1. waitAfter left
  2. temperaturecooled
  3. washwashed three times with water
  4. dry with materialdried with sodium sulfate
  5. customThe drying agent was removed through filtration
  6. customthe solvent was evaporated off under reduced pressure
  7. customThe residue was purified through silica gel column chromatography (NH Biotage Column, ethyl acetate/hexane=from 0% to 80%, gradient)

Sources & evidence

ORD record
ord-1480034a40e34cbeb3629faf2537c67d
Source dataset
uspto-grants-2013_04
Patent number
US08420823B2

Reaction notes

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