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

HRID 1916544
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HRID 1916544 반응식
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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 178418476HCID 178418476, 화합물촉매
HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-07cd0e9a4ced487dae30e68ad4b8edc2
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08618132B2

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