(1-Bromo-2,2-dimethoxyethyl)benzene → 8-(5-Phenylthiazol-2-ylamino)-1,2,3,4-tetrahydronaphthalen-2-ol

Participants

Reaction Steps

A mixture of the product of Example 24A (200 mg, 0.594 mmol) and the product of Example 24B (146 mg, 0.596 mmol) was refluxed for 2 hours in a mixture of EtOH (6 mL) and 1N HCl (1 mL). After cooling to room temperature, the mixture was quenched with saturated NaHCO3 solution and was extracted with EtOAc. The extracts were dried over Na2SO4, filtered evaporated under reduced pressure, and chromatographed on silica gel (95:5 to 92:8 CH2Cl2:CH3OH eluant). The title compound was afforded as a pale tan solid, 53 mg (28%). 1H NMR (DMSO-d6) δ 9.29 (s, 1H), 7.57 (m, 2H), 7.46-7.49 (m, 2H), 7.33-7.38 (m, 2H), 7.22 (m, 1H), 7.10 (m, 1H), 6.88 (d, J=7.4 Hz, 1H), 4.82 (d, J=4.0 Hz, 1H), 3.82 (m, 1H), 2.71-2.98 (m, 4H), 1.83-1.93 (m, 1H), 1.57-1.66 (m, 1H). MS (ESI+) m/z 323 (M+H). Anal. calcd. For C19H18N2OS: C, 70.78; H, 5.63; N, 8.69. Found: C, 70.91; H, 5.37; N, 8.33.

Provenance & Evidence