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Triethylamine → 5-(4-Chloro-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-nicotinonitrile

HRID 1916544
Notes
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Reaction equation

HRID 1916544 reaction equation
Cl[C:2]1[N:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:6][C:3]=1[C:4]#[N:5].[CH2:17]([C:21]1[CH:32]=[CH:31][C:24]([CH2:25][N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:23][CH:22]=1)[CH2:18][C:19]#[CH:20].C(N(CC)CC)C>CN(C=O)C.[Cu]I.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>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH:8]=[N:9][C:2]([C:20]#[C:19][CH2:18][CH2:17][C:21]3[CH:32]=[CH:31][C:24]([CH2:25][N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[CH:23][CH:22]=3)=[C:3]([CH:6]=2)[C:4]#[N:5])=[CH:11][CH:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27640422-Chloro-5-(4-chlorophenyl)nicotinonitrileHCID 859698431-(4-But-3-ynyl-benzyl)-pyrrolidine

Product 1

HCID 100025565-(4-Chloro-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-nicotinonitrile

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Under an argon atmosphere 1.9 mg (0.1 mmol) CuI and 7 mg (0.1 mmol) Pd(PPh3)2Cl2 are added to a solution of 50 mg (0.2 mmol) 2-chloro-5-(4-chloro-phenyl)-nicotinonitrile and 43 mg (0.2 mmol) 1-(4-but-3-ynyl-benzyl)-pyrrolidine in 2 mL DMF and 5 mL (20 mmol) triethylamine and the reaction mixture is stirred for 18 h at 50° C. The mixture is evaporated down i. vac., the residue is taken up in water, extracted exhaustively with EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is is purified by HPLC.

Workup

  1. customThe mixture is evaporated down i
  2. extractionextracted exhaustively with EtOAc
  3. dry with materialthe organic phase is dried over Na2SO4
  4. customis is purified by HPLC

Sources & evidence

ORD record
ord-07cd0e9a4ced487dae30e68ad4b8edc2
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