N-(4-Bromo-2-(2,2-dimethoxyethyl)phenyl)tetrahydro-2H-pyran-4-amine → 5-Bromo-1-(tetrahydro-2H-pyran-4-yl)-1H-indole

HRID 1668480Notes

Reaction equation

HRID 1668480 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[C:4]([CH2:15][CH:16](OC)OC)[CH:3]=1>Cl.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]([CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[CH:16]=[CH:15]2

Participants

3

Reactant 1

HCID 59004603N-(4-Bromo-2-(2,2-dimethoxyethyl)phenyl)tetrahydro-2H-pyran-4-amine

Product 1

HCID 590046455-Bromo-1-(tetrahydro-2H-pyran-4-yl)-1H-indoleYield 106.1%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

Compound 87 (168 mg, 0.488 mmol) was dissolved in anhydrous 1M HCl/methanol (10 mL) in a dry argon purged flask, refluxed for 1 hour, concentrated under reduced pressure to yield compound 88 as a pale brown solid (145 mg, 100%). 1H NMR (DMSO-d6) δ 1.77-2.06 (m, 4H), 3.57 (dt, 2H, J=11.4, 2.1 Hz), 3.99 (dd, 2H, J=11.2, 4.0 Hz), 4.59-4.69 (m, 1H), 6.46 (d, 1H, J=3.2 Hz), 7.23 (dd, 1H, J=8.9, 2.1 Hz), 7.57-7.60 (m, 2H), 7.73 (d, 1H, J=1.8 Hz). ESI-MS (m/z, %): 280/282 (MH+, 100%).

Workup

  1. temperaturerefluxed for 1 hour
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-11e42b169c344421a580e2f7d1582374
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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