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

HRID 1879962Notes

Reaction equation

HRID 1879962 reaction equation
[Br:1][C:2]1[CH:15]=[N:14][C:5]2[NH:6][C:7](=O)[C:8]([CH3:12])([CH3:11])[CH2:9][O:10][C:4]=2[CH:3]=1>C1COCC1>[Br:1][C:2]1[CH:15]=[N:14][C:5]2[NH:6][CH2:7][C:8]([CH3:11])([CH3:12])[CH2:9][O:10][C:4]=2[CH:3]=1

Participants

3

Reactant 1

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

Product 1

HCID 593328368-Bromo-3,3-dimethyl-2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepineYield 44.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-bromo-7,7-dimethyl-6,7-dihydro-9H-5-oxa-1,9-diaza-benzocyclohepten-8-one (620 mg, 2.28 mmol) in THF (15 mL) was added BH3 (9.1 mL of a 1 M solution in THF, 9.1 mmol), and the mixture was heated to reflux overnight. After cooling, the solvent was removed in vacuo. The residue was dissolved in MeOH (15 mL) and 2 N NaOH (5 mL), and the mixture was heated to reflux for 4 h. Methanol was then removed in vacuo and the resulting precipitate was collected by filtration to give the title compound (260 mg, 44%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.78 (d, J=1.8 Hz, 1H), 7.19-7.18 (m, 1H), 4.60 (br s, 1H), 3.83 (s, 2H), 3.10 (d, J=3.9 Hz, 2H), 1.03 (s, 6H); ESI MS m/e 257 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. temperatureAfter cooling
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in MeOH (15 mL)
  6. temperature2 N NaOH (5 mL), and the mixture was heated
  7. temperatureto reflux for 4 h
  8. customMethanol was then removed in vacuo
  9. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-c5446add4a4b4694b36f12fc9a9f46f0
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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