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

HRID 1044413Notes

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

Participants

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

washwashed with sat. NaHCO3
dry with materialdried (Na2SO4)
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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