Sodium hydride → 7-bromo-1H,2H,3H,5H-pyrido(2,3-e)(1,4)oxazepin-2-one

HRID 712628Notes

Reaction equation

HRID 712628 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][CH2:7][C:8]1[C:9]([NH2:15])=[N:10][CH:11]=[C:12]([Br:14])[CH:13]=1)C.[H-].[Na+]>CS(C)=O>[Br:14][C:12]1[CH:11]=[N:10][C:9]2[NH:15][C:4](=[O:3])[CH2:5][O:6][CH2:7][C:8]=2[CH:13]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 57742064(2-Amino-5-bromo-pyridin-3-ylmethoxy)-acetic acid ethyl ester

Product 1

HCID 159260057-bromo-1H,2H,3H,5H-pyrido(2,3-e)(1,4)oxazepin-2-oneYield 64.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(2-Amino-5-bromo-pyridin-3-ylmethoxy)-acetic acid ethyl ester (381 mg, 1.3 mmol) is dissolved in 15 mL of DMSO and 60% sodium hydride (53 mg, 1.3 mmol) is added. The mixture is stirred for 4 hrs and then ice-cold water (100 mL) is added into reaction. The solid formed is filtered and rinsed with more water (2×50 mL) and 50% EtOAc in heptane (30 mL). Then it is dried to give 205 mg of 3-bromo-5,9-dihydro-6-oxa-1,9-diaza-benzocyclohepten-8-one which is used without purification.

Workup

  1. customThe solid formed
  2. filtrationis filtered
  3. washrinsed with more water (2×50 mL) and 50% EtOAc in heptane (30 mL)
  4. customThen it is dried

Sources & evidence

ORD record
ord-d9934b2c88354e5d9d198ffa054f09f0
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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