Trimethylsilylacetylene → HCID 86661617, compound

Participants

Reaction Steps

Sonogashira coupling of bromide 52 (see Example 2F) (0.310 g, 0.873 mmol) and ethynyltrimethylsilane (0.61 mL, 4.3 mmol) at room temperature for 18 h, followed by desilylation with TBAF, as in Example 2U, gave (6S)-6-[(6-ethynyl-3-pyridinyl)methoxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (130) (0.150 g, 57%) as a white solid: mp 168-170° C.; 1H NMR [(CD3)2SO] δ 8.51 (d, J=1.6 Hz, 1H), 8.02 (s, 1H), 7.74 (dd, J=8.0, 2.2 Hz, 1H), 7.54 (dd, J=8.0, 0.6 Hz, 1H), 4.73 (d, J=12.6 Hz, 1H), 4.70 (d, J=12.6 Hz, 1H), 4.67 (dt, J=12.3, 2.3 Hz, 1H), 4.47 (d, J=11.9 Hz, 1H), 4.29 (s, 1H), 4.20-4.28 (m, 3H). APCI MS m/z 301 [M+H]+.

Provenance & Evidence