Potassium Phosphate, Tribasic → 1-(benzothiazol-6-yl)-3-(1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-pyrrolo [2,3-b]pyridin-5-yl)imidazolidin-2-one

HRID 80252Notes

Reaction equation

HRID 80252 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][NH:12][C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Br[C:17]1[CH:18]=[C:19]2[CH:25]=[CH:24][N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:20]2=[N:21][CH:22]=1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:17]4[CH:18]=[C:19]5[CH:25]=[CH:24][N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:20]5=[N:21][CH:22]=4)[C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 598250161H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-HCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

Product 1

HCID 596361831-(benzothiazol-6-yl)-3-(1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-pyrrolo [2,3-b]pyridin-5-yl)imidazolidin-2-oneYield 52.5%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

1-Benzothiazol-6-yl-imidazolidin-2-one (I-84b: 0.2 g, 0.9 mmol) was reacted with 5-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (I-187a: 0.32 g, 1.0 mmol), 1,4-dioxane (15 mL), copper iodide (0.052 g, 0.2 mmol), trans N,N′-dimethyl-cyclohexane-1,2-diamine (0.038 g, 0.27 mmol) and potassium phosphate (0.65 g, 2.2 mmol) to afford the crude product. Purification by column chromatography on silica gel (1.5% methanol in DCM) afforded 0.22 g of the product (52.3% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1.5% methanol in DCM)

Sources & evidence

ORD record
ord-2470d95cef534ee0874d152d3bb4e5bc
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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