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Iodide Ion → HCID 67483971, compound

HRID 1936268
Notes
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Reaction equation

HRID 1936268 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]([C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[C:19]([C:21]1[CH:22]=[N:23][CH:24]=[N:25][CH:26]=1)#[CH:20].[I-]>CN(C)C=O.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.C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:18])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:20]#[C:19][C:21]2[CH:22]=[N:23][CH:24]=[N:25][CH:26]=2)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 30165Iodide IonHCID 14751945-EthynylpyrimidineHCID 674834473-Cyclopentyl-2-(4-iodo-phenyl)-propionic acid methyl ester

Product 1

HCID 67483971HCID 67483971, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalyst
HCID 6102075
Dichlorobis(triphenylphosphine)palladium
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid methyl ester (719 mg, 2.01 mmol) and triethylamine (3 mL, 0.015 mmol) in N,N-dimethylformamide (3 mL) was treated with 5-ethynyl-pyrimidine (230 mg, 2.21 mmol). The resulting reaction mixture was degassed with argon for 10 min and then treated with cooper iodide (92 mg, 0.48 mmol) and bis(triphenylphosphine)palladium (II) chloride (169 mg, 0.24 mmol). The reaction was stirred at 25° C. for 18 h and then heated at 67° C. for 2 h. At this time, the reaction was cooled to 25° C. and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-pyrimidin-5-ylethynyl-phenyl)-propionic acid methyl ester (440 mg, 66%) as an orange oil: EI-HRMS m/e calcd for C21H22N2O2 (M+) 334.1681, found 334.1681.

Workup

  1. customThe resulting reaction mixture
  2. customwas degassed with argon for 10 min
  3. temperatureheated at 67° C. for 2 h
  4. temperatureAt this time, the reaction was cooled to 25° C.
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b88a8aedf93346448d167ff5232bfe77
Source dataset
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06388071B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes