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

HRID 2117135Notes

Reaction equation

HRID 2117135 reaction equation
[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(C(C)C)=CC(C(C)C)=CC=2C(C)C)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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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-i-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.

Workup

  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)

Sources & evidence

ORD record
ord-6b541f3090e84821bc37b337bd462906
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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