Propargyl alcohol → HCID 58485522, compound

HRID 2179605Notes

Reaction equation

HRID 2179605 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C@@H:4]([NH:10][C:11]([C:13]1[S:14][C:15]3[CH:21]=[C:20](Br)[CH:19]=[CH:18][C:16]=3[CH:17]=1)=[O:12])[CH2:3]2.[CH2:23]([OH:26])[C:24]#[CH:25]>C(N(CC)CC)C.CN(C=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.[Cu]I>[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C@@H:4]([NH:10][C:11]([C:13]1[S:14][C:15]3[CH:21]=[C:20]([C:25]#[C:24][CH2:23][OH:26])[CH:19]=[CH:18][C:16]=3[CH:17]=1)=[O:12])[CH2:3]2

Participants

6

Reactant 2

HCID 7859Propargyl alcoholHCID 66904783HCID 66904783, compound

Product 1

HCID 58485522HCID 58485522, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 22056947triethylamine N,N-dimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

120 mg (0.30 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromo-1-benzothiophene-2-carboxamide hydrochloride (Example 11A), 10.5 mg (0.01 mmol) of PdCl2(PPh3)2 and 4.6 mg (0.02 mmol) of copper(I) iodide are dissolved in 1.5 ml of triethylamine/DMF (2:1) under argon and stirred at 60° C. for 1 h. Addition of 25.1 mg (0.45 mmol) of propargyl alcohol is followed by heating at 70° C. for a further 16 h. Cooling is followed by filtration through kieselguhr and purification by preparative HPLC, concentration and drying of the product under high vacuum. 12 mg (11% of theory) of the title compound are obtained.

Workup

  1. temperatureby heating at 70° C. for a further 16 h
  2. temperatureCooling
  3. filtrationis followed by filtration through kieselguhr and purification by preparative HPLC, concentration
  4. customdrying of the product under high vacuum

Sources & evidence

ORD record
ord-a94034e77dbd43998ac27b62dbe5f3cd
Source dataset
uspto-grants-2015_06
Patent number
US09067931B2

Reaction notes

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