HCID 71295661, compound → HCID 71295500, compound

HRID 1776845Notes

Reaction equation

HRID 1776845 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][CH2:7][CH:8]([OH:19])[CH2:9][N:10]3[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[CH:12]=[C:11]3[C:4]=2[CH:3]=1>C(Cl)Cl.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][CH2:7][C:8](=[O:19])[CH2:9][N:10]3[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[CH:12]=[C:11]3[C:4]=2[CH:3]=1

Participants

5

Reactant 1

HCID 71295661HCID 71295661, compound

Product 1

HCID 71295500HCID 71295500, compoundYield 70.4%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 24477Sodium ThiosulfateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

DMP (742 mg, 1.749 mmol) was added to the solution of 2-bromo-7,8-dihydro-6H-benzo[2,3][1,5]oxazocino[5,4-a]indol-7-ol (500 mg, 1.46 mmol) in CH2Cl2 (5 mL) at 0° C. The mixture was stirred at room temperature overnight. The mixture was then diluted with saturated Na2S2O3 and NaHCO3 (30 mL, 30 mL). The mixture was extracted with ethyl acetate (20 mL×3). The organic layer was washed with brine (30 mL×3), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using prep-TLC (petroleum ether:EA=3:1) to provide 2-bromo-6H-benzo[2,3][1,5]oxazocino[5,4-a]indol-7(8H)-one (350 mg, yield: 70.4%). 1H-NMR (CDCl3, 400 MHz) δ 7.55˜7.68 (m, 2H), 7.53 (t, J=6.0 Hz, 1H), 7.35˜7.37 (m, 1H), 7.28˜7.30 (m, 1H), 7.17˜7.24 (m, 1H), 7.08 (t, J=8.4 Hz, 1H), 6.70 (d, J=0.8 Hz, 1H), 4.73 (s, 2H), 4.55 (s, 2H). MS (M+H)+: 342/344.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (20 mL×3)
  2. washThe organic layer was washed with brine (30 mL×3)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified

Sources & evidence

ORD record
ord-f240e6238bac40df89ad7846f389d27d
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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