Cesium carbonate → Tert-butyl 2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)ethyl(methyl)carbamate

HRID 1774656Notes

Reaction equation

HRID 1774656 reaction equation
CC1C=CC(S([O:11][CH2:12][CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:15])(=O)=O)=CC=1.[Br:23][C:24]1[CH:25]=[C:26]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35](O)[N:34]=2)[C:27](=[O:31])[N:28]([CH3:30])[CH:29]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Br:23][C:24]1[CH:25]=[C:26]([NH:32][C:33]2[N:34]=[C:35]([O:11][CH2:12][CH2:13][N:14]([CH3:15])[C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH:36]=[CH:37][CH:38]=2)[C:27](=[O:31])[N:28]([CH3:30])[CH:29]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 215811562-(tert-Butoxycarbonyl(methyl)amino)-ethyl 4-methylbenzenesulfonateHCID 178479984HCID 178479984, compound

Product 1

HCID 118116879Tert-butyl 2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)ethyl(methyl)carbamateYield 22.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 112b (3.3 g, 10 mmol), 5-Bromo-3-(6-hydroxypyridin-2-ylamino)-1-methylpyridin-2(1H)-one 101a (7.4 g, 25 mmol) and Cs2CO3 (4.1 g, 12.5 mmol) in DMF (40 mL) was stirred at 100° C. for 4 h. The mixture partitioned between EA and water. The organic layer was separated, dried over Na2SO4, filtered and concentrated to give tert-butyl 2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)ethyl(methyl)carbamate 112c (1.0 g, 22%) as a yellow solid. ESI-LCMS: m/z=454.9

Workup

  1. customThe mixture partitioned between EA and water
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9811cc2079f245bbba64d8e6fb9698d9
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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