Methyl 6-(adamantan-1-ylmethoxy)-5-cyclopropylnicotinate → 4-((3-(((Tert-butyldimethylsilyl)oxy)methyl)adamantan-1-yl)methoxy)-5-chloro-2-fluorobenzoic acid

Participants

Reaction Steps

Following the procedure as described in Example 150 step 4 and making variations as required to replace methyl 6-(adamantan-1-ylmethoxy)-5-cyclopropylnicotinate with methyl 4-((3-(((tert-butyldimethylsilyl)oxy)methyl)adamantan-1-yl)methoxy)-5-chloro-2-fluorobenzoate, the title compound was obtained as a colorless solid (1.02 g, 94%): 1H NMR (300 MHz, DMSO-d6) δ 13.03 (br s, 1H), 7.79 (d, J=7.7 Hz, 1H), 7.12 (d, J=12.7 Hz, 1H), 3.70 (s, 2H), 3.12 (s, 2H), 2.05-1.96 (m, 2H), 1.63-1.42 (m, 6H), 1.41-1.27 (m, 6H), 0.81 (s, 9H), −0.05 (s, 6H); MS (ES+) m/z 483.1, 485.1 (M+1).

Provenance & Evidence