Methyl 6-(bromomethyl)pyridine-2-carboxylate → (1R,2S)-6-((2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)methyl)picolinic acid

Participants

Reaction Steps

The title compound was prepared in analogy to Example 1 starting from 6-bromomethyl-pyridine-2-carboxylic acid methyl ester (commercially available), (1R,2S) and (1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C23H17ClN2O3: 404, observed (M+H)+: 405.2 1H NMR (400 MHz, DMSO-d6) δppm 2.12 (dd, J=9.09, 4.80 Hz, 1 H) 2.39 (dd, J=8.08, 4.80 Hz, 1 H) 3.22 (t, J=8.59 Hz, 1 H) 5.14 (s, 2 H) 6.15 (d, J=7.33 Hz, 1 H) 6.73 (t, J=7.45 Hz, 1 H) 6.88 (d, J=7.58 Hz, 1 H) 7.00-7.10 (m, 1 H) 7.26 (d, J=1.01 Hz, 1 H) 7.38 (s, 4 H) 7.84-7.98 (m, 2 H).

Provenance & Evidence