Triethylamine → HCID 10388351, compound

HRID 1916550Notes

Reaction equation

HRID 1916550 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)=[C:26]([Cl:38])[CH:25]=1>CN(C=O)C.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[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[CH2:32][CH2:33][CH2:34][CH2:35]4)=[C:26]([Cl:38])[CH:25]=3)=[N:19][CH:20]=2)=[CH:13][CH:14]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 803776HCID 803776, compoundHCID 578453285-(4-Chloro-phenyl)-2-ethynyl-pyridine

Product 1

HCID 10388351HCID 10388351, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Under an argon atmosphere 0.14 mL (1.00 mmol) triethylamine, 11 mg (0.02 mmol) Pd(PPh3)2Cl2 and 2.9 mg (0.015 mmol) CuI are added successively to a solution of 71 mg (0.33 mmol) 5-(4-chloro-phenyl)-2-ethynyl-pyridine and 100 mg (0.33 mmol) 1-[2-(4-bromo-2-chloro-phenoxy)-ethyl]-pyrrolidine in 3.0 mL DMF. The mixture is stirred for 10 min at 100° C. and at 200 Watt in the microwave. The reaction solution is diluted with 30 mL EtOAc, washed twice with semisaturated NaCl solution and the organic phase is dried over MgSO4. The solvent is eliminated i.vac. and further purification is carried out by column chromatography with HPLC-MS.

Workup

  1. washwashed twice with semisaturated NaCl solution
  2. dry with materialthe organic phase is dried over MgSO4
  3. customand further purification

Sources & evidence

ORD record
ord-9cc22603ea594e348b2035e170d48371
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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