Triethylamine → HCID 10046847, compound

HRID 1916570Notes

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

Participants

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

extractionthe aqueous phase is extracted with 20 mL EtOAc
extractionThe organic phase is extracted with saturated NaCl solution
dry with materialdried over Na2SO4
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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