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Sodium Carbonate → 2-{4-[2-(4-Methyl-piperidin-1-yl)-ethoxy]-phenylethynyl}-5-phenyl-pyridine

HRID 271712
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HRID 271712 반응식
[C:1]1(OB(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:12]1[CH:13]=[CH:14][C:15]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]3[CH2:34][CH2:33][CH:32]([CH3:35])[CH2:31][CH2:30]3)=[CH:22][CH:21]=2)=[N:16][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CO.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:35][CH:32]1[CH2:33][CH2:34][N:29]([CH2:28][CH2:27][O:26][C:23]2[CH:24]=[CH:25][C:20]([C:19]#[C:18][C:15]3[CH:14]=[CH:13][C:12]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:17][N:16]=3)=[CH:21][CH:22]=2)[CH2:30][CH2:31]1
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참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 690601725-Bromo-2-{4-[2-(4-methylpiperidin-1-yl)ethoxy]phenylethynyl}pyridine

생성물 1

HCID 598357442-{4-[2-(4-Methyl-piperidin-1-yl)-ethoxy]-phenylethynyl}-5-phenyl-pyridine

시약·촉매·용매 4

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 887Methanol용매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

Under an argon atmosphere 30 mg (0.25 mmol) phenylboric acid are added to a solution of 100 mg (0.25 mmol) 5-bromo-2-{4-[2-(4-methyl-piperidin-1-yl)-ethoxy]-phenylethynyl}-pyridine, 0.25 mL (0.50 mmol) of a 2 M Na2CO3 solution and 4 mg (0.01 mmol) Pd(dppf)Cl2 in 5 mL 1,4-dioxane and 2 mL MeOH. The reaction mixture is stirred for 3 days at 90° C. The reaction mixture is diluted with EtOAc and the organic phase is washed with 40 mL water and finally with saturated NaCl solution. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The purification is carried out using HPLC-MS and by column chromatography on silica gel (gradient: DCM/MeOH/NH3 95:5:0.5 to DCM/MeOH/NH3 9:1:0.1).

후처리

  1. washthe organic phase is washed with 40 mL water and finally with saturated NaCl solution
  2. dry with materialThe organic phase is dried over MgSO4
  3. customThe purification

출처 및 근거

ORD 기록
ord-4f7947abfcbd4537b04dd71808da0a2c
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07452911B2

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