Triphenylphosphine → 5-(3-Amino-6-chloro-pyridin-2-yl)-2,2-dimethyl-pent-4-ynoic acid ethyl ester

HRID 1713423Notes

Reaction equation

HRID 1713423 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:20][C:21]1[N:26]=[C:25](I)[C:24]([NH2:28])=[CH:23][CH:22]=1.[CH2:29]([O:31][C:32](=[O:39])[C:33]([CH3:38])([CH3:37])[CH2:34][C:35]#[CH:36])[CH3:30]>CCN(CC)CC.Cl[Pd]Cl.[Cu]I>[CH2:29]([O:31][C:32](=[O:39])[C:33]([CH3:38])([CH3:37])[CH2:34][C:35]#[C:36][C:25]1[C:24]([NH2:28])=[CH:23][CH:22]=[C:21]([Cl:20])[N:26]=1)[CH3:30]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 14459632Ethyl 2,2-dimethylpent-4-ynoateHCID 184070436-Chloro-2-iodopyridin-3-amine

Product 1

HCID 597547775-(3-Amino-6-chloro-pyridin-2-yl)-2,2-dimethyl-pent-4-ynoic acid ethyl ester

Reagents, catalysts & solvents 3

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

Procedure

PdCl2 (0.200 g, 1.13 mmol), CuI (0.214 g, 1.13 mmol), and PPh3 (0.590, 2.25 mmol) were suspended in NEt3 (150 mL) and stirred under N2. 6-Chloro-2-iodo-pyridin-3-ylamine (5.7 g, 2.24 mmol) was added, followed by 2,2-dimethyl-pent-4-ynoic acid ethyl ester (5.2 g, 3.37 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-b342a94e4ec44858b4b0ddfe89796f83
Source dataset
uspto-grants-2010_09
Patent number
US07795274B2

Reaction notes

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