Potassium Phosphate, Tribasic → 4-Chloro-2-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

HRID 347530노트

반응식

HRID 347530 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:9](B(O)O)=[CH:10][C:3]=12.I[C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(CCC)=CC(CCC)=CC=2CCC)CCCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:9]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[CH:10][C:3]=12

참가 물질

8

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 707143-IodopyridineHCID 21081673(4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-2-yl)boronic acid

생성물 1

HCID 210816764-Chloro-2-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine수율 52.3%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 21081571Dicyclohexyl(2',4',6'-tripropyl-[1,1'-biphenyl]-2-yl)phosphine촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

Argon was bubbled through a mixture of 4-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-2-ylboronic acid (5.55 g, 17 mmol), 3-iodopyridine (6.97 g, 34 mmol), Pd(OAc)2, 2-dicyclohexylphosphino-2′,4′,6′-tri-1-propyl-1,1′-biphenyl (405 mg, 0.85 mmol), and K3PO4 (2 M in H2O, 34 mmol) in DME (50 mL) for 10 min and then heated at reflux overnight. The reaction mixture was diluted with EtOAc and washed with saturated aq. K2HPO4 solution. The title compound was purified by flash column chromatography (silica gel, 20% EtOAc/CH2Cl2) to afford the desired product (3.2 g, 52% yield) as an oil. LC/MS(ESI+) m/z 361 (M+H)+.

후처리

  1. temperatureheated
  2. temperatureat reflux overnight
  3. washwashed with saturated aq. K2HPO4 solution
  4. customThe title compound was purified by flash column chromatography (silica gel, 20% EtOAc/CH2Cl2)

출처 및 근거

ORD 기록
ord-083f4f23d8fc443688e30f2d2eb94193
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173031B2

반응 노트

불러오는 중…