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Triethylamine → HCID 10046847, compound

HRID 1916570
Notes
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Reaction equation

HRID 1916570 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]#[CH:22])=[N:19][CH:20]=2)=[CH:11][CH:10]=1.Br[C:24]1[CH:25]=[N:26][C:27]([O:30][CH2:31][CH2:32][N:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)=[N:28][CH:29]=1>CN(C=O)C.O.[Cu]I>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]#[C:22][C:24]3[CH:29]=[N:28][C:27]([O:30][CH2:31][CH2:32][N:33]4[CH2:37][CH2:36][CH2:35][CH2:34]4)=[N:26][CH:25]=3)=[N:19][CH:20]=2)=[CH:13][CH:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 578453285-(4-Chloro-phenyl)-2-ethynyl-pyridineHCID 638675465-Bromo-2-(2-pyrrolidin-1-yl-ethoxy)-pyrimidine

Product 1

HCID 10046847HCID 10046847, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Under an argon atmosphere 0.11 mL (0.79 mmol) triethylamine, 7 mg (0.01 mmol) tetrakis-triphenylphosphane-palladium and 1.3 mg (0.01 mmol) CuI are added successively to a solution of 56 mg (0.26 mmol) 5-(4-chloro-phenyl)-2-ethynyl-pyridine and 71 mg (0.26 mmol) 5-bromo-2-(2-pyrrolidin-1-yl-ethoxy)-pyrimidine in 3.0 mL DMF. The mixture is stirred for 20 min at 100° C. and at 300 Watt in the microwave. The reaction solution is diluted with 10 mL water and the aqueous phase is extracted with 20 mL EtOAc. The organic phase is extracted with saturated NaCl solution and dried over Na2SO4. The solvent is eliminated i.vac. and further purification is carried out by column chromatography with HPLC-MS.

Workup

  1. extractionthe aqueous phase is extracted with 20 mL EtOAc
  2. extractionThe organic phase is extracted with saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. customand further purification

Sources & evidence

ORD record
ord-3869cf6be98a4e3699f8f8165b38f8f4
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08618132B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes