Triethylamine → HCID 15296876, compound

HRID 129613Notes

Reaction equation

HRID 129613 reaction equation
[CH2:1]([C:4]1([CH2:16][CH2:17][CH3:18])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]#[CH:15])[CH:12]=2)[S:7][CH2:6][CH2:5]1)[CH2:2][CH3:3].C(N(CC)CC)C.I[C:27]1[CH:37]=[CH:36][C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:29][CH:28]=1>[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH2:16]([C:4]1([CH2:1][CH2:2][CH3:3])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]#[C:15][C:27]3[CH:37]=[CH:36][C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:29][CH:28]=3)[CH:12]=2)[S:7][CH2:6][CH2:5]1)[CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 142891Ethyl 4-iodobenzoate2×HCID 15895301HCID 15895301, compound2×

Product 1

HCID 15296876HCID 15296876, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
55 °C

Procedure

A mixture of 0.338 g (1.47 mmol) of 4,4-dipropylthiochroman-6-yl)acetylene (Compound 31), 24 mg, (0.13 mmol) of copper (I) iodide, and 2.54 g (25 mmol of triethylamine were degassed with argon for 15 minutes. To the suspension was added 0.57 g (2.07 mmol) of ethyl 4-iodobenzoate (Compound 22) and then 0.12 g (0.17 mmol) of bis(triphenylphosphine)palladium (II) chloride. The suspension was degassed with argon for an additional 5 minutes, the tube was sealed and the mixture stirred at 55° C. for 16 hours.

Workup

  1. customwere degassed with argon for 15 minutes
  2. customThe suspension was degassed with argon for an additional 5 minutes
  3. customthe tube was sealed

Sources & evidence

ORD record
ord-9b8d0b5af6a741c6be22571f48176e87
Source dataset
uspto-grants-1995_11
Patent number
US05468879

Reaction notes

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