Triethylamine → HCID 10386529, compound

HRID 271658Notes

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.Cl[C:24]1[N:25]=[N:26][C:27]([O:30][CH2:31][CH2:32][N:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)=[CH: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[N:25]=[N:26][C:27]([O:30][CH2:31][CH2:32][N:33]4[CH2:34][CH2:35][CH2:36][CH2:37]4)=[CH:28][CH:29]=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, 4 mg (0.01 mmol) chlorine(di-2-norbornylphosphino)(2′-dimethylamino-1-1′-biphenyl-2-yl)palladium(II) and 1.2 mg (0.01 mmol) CuI are added successively to a solution of 57 mg (0.27 mmol) 5-(4-chloro-phenyl)-2-ethynyl-pyridine and 61 mg (0.26 mmol) 3-chloro-6-(2-pyrrolidin-1-yl-ethoxy)-pyridazine in 3.0 mL DMF. The mixture is stirred for 20 min at 100° C. and 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-8eae506635af48b6ac4bb1e53b582776
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452911B2

Reaction notes

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