Triethylamine → HCID 10388352, compound

HRID 271653Notes

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:37]=[CH:36][C:27]([O:28][CH2:29][CH2:30][N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:26][C:25]=1[Cl:38]>CN(C=O)C.CCOC(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:37]=[CH:36][C:27]([O:28][CH2:29][CH2:30][N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[CH:26][C:25]=3[Cl:38])=[N:19][CH:20]=2)=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Under an argon atmosphere 0.13 mL (1.00 mmol) triethylamine, 22 mg (0.02 mmol) tetrakis-triphenylphosphane-palladium and 3.7 mg (0.02 mmol) CuI are added successively to a solution of 80 mg (0.37 mmol) 5-(4-chloro-phenyl)-2-ethynyl-pyridine and 114 mg (0.37 mmol) 1-[2-(4-bromo-3-chloro-phenoxy)-ethyl]-pyrrolidine in 3.0 mL DMF. The mixture is stirred for 15 min at 100° C. and at 200 W in the microwave. The reaction solution is diluted with 40 mL EtOAc, washed twice with semisaturated NaHCO3 solution and the organic phase is dried over MgSO4. The solvent is eliminated i.vac. and the residue is triturated with tert-butylmethylether. The solvent is eliminated i.vac. and further purification is carried out by column chromatography with HPLC-MS.

Workup

washwashed twice with semisaturated NaHCO3 solution
dry with materialthe organic phase is dried over MgSO4
customand the residue is triturated with tert-butylmethylether
customand further purification

Sources & evidence

ORD record: ord-02cf6498e1ba4f158d8b094e30a7d696
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452911B2

Reaction notes

Loading…