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Potassium Phosphate, Tribasic → 4-chloro-1-(3-methoxy-4-((2-(trimethylsilyl)ethoxy)methoxy)phenyl)pyridin-2(1H)-one

HRID 1044413
Notes
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Reaction equation

HRID 1044413 reaction equation
CNC1CCCCC1NC.[Cl:11][C:12]1[CH:17]=[CH:16][NH:15][C:14](=[O:18])[CH:13]=1.Br[C:20]1[CH:34]=[CH:33][C:23]([O:24][CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])=[C:22]([O:35][CH3:36])[CH:21]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(Cl)Cl.[Cu]I>[Cl:11][C:12]1[CH:17]=[CH:16][N:15]([C:20]2[CH:34]=[CH:33][C:23]([O:24][CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:31])([CH3:30])[CH3:32])=[C:22]([O:35][CH3:36])[CH:21]=2)[C:14](=[O:18])[CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 27576114-Chloropyridin-2-olHCID 60083834(2-((4-Bromo-2-methoxyphenoxy)methoxy)ethyl)trimethylsilane

Product 1

HCID 585802544-chloro-1-(3-methoxy-4-((2-(trimethylsilyl)ethoxy)methoxy)phenyl)pyridin-2(1H)-oneYield 81%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

N1,N2-dimethylcyclohexane-1,2-diamine (140 μL, 0.81 mmol) was added to a mixture of commercially available 4-chloropyridin-2(1H)-one (150 mg, 1.16 mmol), (2-((4-bromo-2-methoxyphenoxy)methoxy)ethyl)trimethylsilane (463 mg, 1.39 mmol), preparation described in Part G of Procedure 1, K3PO4 (737 mg, 3.47 mmol), and Copper (I) Iodide (154 mg, 0.81 mmol) in Dioxane (6 mL). The mixture was stirred at 100° C. overnight. The reaction was diluted with DCM, washed with sat. NaHCO3, dried (Na2SO4), and concentrated. The crude was subjected to ISCO flash chromatography (silica gel/hexanes/ethyl acetate 100:0 to 0:100 gradient) to afford the desired product 4-chloro-1-(3-methoxy-4-((2-(trimethylsilyl)ethoxy)methoxy)phenyl)pyridin-2(1H)-one 14A (358 mg, 0.94 mmol, 81% yield) as a light yellow solid. LC/MS 382 (M+H)+, tR 1.06 min (method 5).

Workup

  1. washwashed with sat. NaHCO3
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bc028f3d5ed7404d898a2c375d363ad5
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08563583B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes