Triphenylphosphine → HCID 59754768, compound

HRID 1713427Notes

Reaction equation

HRID 1713427 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.I[C:21]1[C:26]([NH2:27])=[CH:25][CH:24]=[C:23]([O:28][CH3:29])[N:22]=1.[CH2:30]([O:32][C:33](=[O:40])[C:34]([CH3:39])([CH3:38])[CH2:35][C:36]#[CH:37])[CH3:31]>CCN(CC)CC.Cl[Pd]Cl.[Cu]I>[CH2:30]([O:32][C:33](=[O:40])[C:34]([CH3:39])([CH3:38])[CH2:35][C:36]#[C:37][C:21]1[C:26]([NH2:27])=[CH:25][CH:24]=[C:23]([O:28][CH3:29])[N:22]=1)[CH3:31]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 14459632Ethyl 2,2-dimethylpent-4-ynoateHCID 59754770HCID 59754770, compound

Product 1

HCID 59754768HCID 59754768, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

PdCl2 (0.059 g, 0.33 mmol), CuI (0.063 g, 0.33 mmol), and PPh3 (0.173 g, 0.66 mmol) were suspended in NEt3 (40 mL) and stirred under N2. 2-Iodo-6-methoxy-pyridin-3-ylamine (1.65 g, 6.60 mmol) was added, followed by 2,2-dimethyl-pent-4-ynoic acid ethyl ester (Example 4, Step 1; 1.22 g, 7.91 mmol), and the reaction was stirred overnight at room temperature. The reaction mixture was concentrated and purified on silica gel (0-50% EtOAc in hexanes) to give the desired product.

Workup

  1. stirringthe reaction was stirred overnight at room temperature
  2. concentrationThe reaction mixture was concentrated
  3. custompurified on silica gel (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-75db9693f576405e9aeefbd16c408dfe
Source dataset
uspto-grants-2010_09
Patent number
US07795274B2

Reaction notes

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