Br[CH2:2][CH2:3][CH2:4][C:5]1[N:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:8][C:9]=1[CH3:10].CN1C(=O)N(C)[CH2:21][CH2:20]C1.[C-]#[C-].[CH3:28][Si:29]([Li])([CH3:31])[CH3:30]>C1COCC1>[CH3:10][C:9]1[O:8][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6][C:5]=1[CH2:4][CH2:3][CH2:2][C:20]#[C:21][Si:29]([CH3:31])([CH3:30])[CH3:28]Bromide 1-5 (3.2 g, 12.2 mmol) was dissolved in a 1:1 mixture of THF:DMPU (200 mL) and cooled to 0° C. under N2 atmosphere. Trimethylsilyl lithium acetylide (50mL, 25 mmol) was added to the solution via syringe and allowed to equilibrate to 23° C. for 16 hours. The solution was partitioned between water and EtOAc in a separatory funnel. Organic layer was washed with water, brine, and dried over MgSO4. Solvent removed in vacuo and residue chromatographed with 5% EtOAc/hexanes to give 1.9 g of the product as a clear oil (50% yield). NMR CDCl3 (δ): 7.82 (2H, m); 7.27 (3H, m);2.46 (2H, m); 2.20 (3H, s); 2.10 (2H, m); 1.76 (2H, m); 0.01 (9H, s). M+1=298.1
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