(3-Bromopropoxy)(tert-butyl)dimethylsilane → HCID 58914709, compound

Participants

Reaction Steps

Using a method similar to Example 37, with 3-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1-(2-chloro-benzyl)-1,3-dihydro-indol-2-one (150 mg, 0.31 mmol), a 0.5M solution of potassium bis(trimethylsilyl)amide (0.622 mL, 0.31 mmol), and (3-bromopropoxy)-tert-butyldimethylsilane (0.072 mL, 0.31 mmol) in DMF (3 mL) followed by treatment with TBAF (0.70 mL, 0.70 mmol) gives a crude brown gum. Purify by flash chromatography (gradient of 25% EtOAc/hexanes to 50% EtOAc/hexanes) to give 68 mg (51%) of the title compound as a pink solid. MS (ES): m/z=436 (M+1), 434 (M−1); 1H NMR(DMSO-d6): δ8.23 (s, 1H), 7.54 (dd, J=1.4 Hz, J=7.7 Hz, 1H), 7.37-7.22 (m, 4H), 7.12-7.04 (m, 2H), 6.90 (d, J=7.7 Hz, 1H), 6.83 (s, 2H), 5.05 (abq, J=16.7, 2H), 3.33 (m, under H2O), 2.27-2.18 (m, 2H), 2.11 (s, 6H), 1.23-0.99 (m, 2H).

Provenance & Evidence