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

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Reaction Steps

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%).

Provenance & Evidence