Sodium hydride → 8-bromo-3,3-dimethyl-2,3-dihydropyrido[3,2-b][1,4]oxazepin-4(5H)-one

HRID 340817Notes

Reaction equation

HRID 340817 reaction equation
C[O:2][C:3](=O)[C:4]([CH3:16])([CH3:15])[CH2:5][O:6][C:7]1[C:8]([NH2:14])=[N:9][CH:10]=[C:11]([Br:13])[CH:12]=1.[H-].[Na+]>CS(C)=O.O>[Br:13][C:11]1[CH:10]=[N:9][C:8]2[NH:14][C:3](=[O:2])[C:4]([CH3:16])([CH3:15])[CH2:5][O:6][C:7]=2[CH:12]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 593328383-(2-Amino-5-bromo-pyridin-3-yloxy)-2,2-dimethylpropionic acid methyl ester

Product 1

HCID 593328468-bromo-3,3-dimethyl-2,3-dihydropyrido[3,2-b][1,4]oxazepin-4(5H)-oneYield 76.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 3-(2-amino-5-bromo-pyridin-3-yloxy)-2,2-dimethylpropionic acid methyl ester (880 mg, 2.90 mmol) in DMSO (40 mL) was added NaH (60% in oil, 139-mg, 3.48 mmol), and the mixture was stirred overnight at room temperature. The mixture was diluted with water (100 mL), and further stirred for 15 min. The resulting precipitate was collected by filtration to give the title compound (600 mg, 76%) as a white solid: 1H NMR (300 MHz, CDCl3) δ8.34 (br s, 1H), 8.11 (d, J=1.8 Hz, 1H), 7.46 (d, J=1.8 Hz, 1H), 4.01 (s, 2H), 1.32 (s, 6H); ESI M Sm/e 271 (M+H)+.

Workup

  1. stirringfurther stirred for 15 min
  2. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-15862f2ebc4d4d7e870d4875685bd789
Source dataset
uspto-grants-2014_11
Patent number
US08895545B2

Reaction notes

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