Pyridine → HCID 178463227, compound

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Reaction Steps

Add MeI (0.623 g, 4.4 mmol) to a solution of N-4-fluorobenzyl-N-methylthioacetamide (0.662 g, 3.4 mmol) in 10 mL of ether at rt. Stir the mixture for 3 h and evaporate the ether under vacuum. Add (6-aminoindan-1-yl)carbamic acid tert-butyl ester (0.7 g, 2.28 mmol) followed by 5 mL of pyridine. Stir the resulting mixture for 12 h. Evaporate pyridine and purify the residue by column chromatography (silica gel, 3% MeOH in CH2Cl2) to give 1.26 g of (6-(1-((4-fluorobenzyl)methylamino)ethylideneamino)indan-1-yl)carbamic acid tert-butyl ester as a light yellow solid; MS 412 (MH+); 1H NMR (CD3OD) d 7.35-7.29 (2H, m), 7.18-7.10 (3H, m), 6.70 (1H, s), 6.65 (1H, d, J=7.6 Hz), 5.06 (1H, t, J=6.8 Hz), 4.69 (2H, s), 3.05 (3H, s), 2.97-2.91 (1H, m), 2.84-2.77 (1H, m), 2.55-2.48 (1H, m), 1.97 (3H, s), 1.52 (9H, s).

Provenance & Evidence