Tetrahydrofuran → HCID 71295566, compound

HRID 1776846Notes

Reaction equation

HRID 1776846 reaction equation
[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.[CH2:22]1COCC1>>[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][CH2:7][C:8]([CH3:22])([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

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 71295500HCID 71295500, compound

Product 1

HCID 71295566HCID 71295566, compoundYield 47.6%

Procedure

MgBrCH3 (0.12 mL, 0.352 mmol) was added to the solution of 2-bromo-6H-benzo[2,3][1,5]oxazocino[5,4-a]indol-7(8H)-one (60 mg, 0.176 mmol) in THF (1 mL) at 0° C. under N2. The mixture was stirred at room temperature for 30 minutes. The mixture was then quenched with saturated NH4Cl (10 mL) and extracted with ethyl acetate (10 mL×3). The organic layer was washed with brine (20 mL), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using p-TLC (petroleum ether:EA=3:1) to provide 2-bromo-7-methyl-7,8-dihydro-6H-benzo[2,3][1,5]oxazocino[5,4-a]indol-7-ol (30 mg, yield: 47.6%). 1H-NMR(CDCl3, 400 MHz) δ 7.56˜7.59 (m, 2H), 7.36˜7.40 (m, 2H), 7.18˜7.22 (m, 1H), 7.08 (t, J=7.2 Hz, 1H), 6.93 (d, J=8.8 Hz, 1H), 6.61 (s, 1H), 3.81˜4.15 (m, 4H), 2.34 (s, 1H), 1.24 (s, 3H). MS (M+H)+: 358/360.

Workup

  1. customThe mixture was then quenched with saturated NH4Cl (10 mL)
  2. extractionextracted with ethyl acetate (10 mL×3)
  3. washThe organic layer was washed with brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified

Sources & evidence

ORD record
ord-a8404214c7854e85b33f1f406d4914f4
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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