Triphenylphosphine → 5-Ethyloxy carbonylimidazo[2,1-b][1,3]thiazol-6-yl-methyl(triphenyl)phosphonium bromide
Reaction equation
[Br:1][CH2:2][C:3]1[N:4]=[C:5]2[N:9]([C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][S:6]2.[C:16]1([P:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[Br-:1].[CH2:14]([O:13][C:11]([C:10]1[N:9]2[C:5]([S:6][CH:7]=[CH:8]2)=[N:4][C:3]=1[CH2:2][P+:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:12])[CH3:15]Participants
4
Procedure
To a stirred suspension of Step 2 intermediate (1.90 g, 6.571 mmol) in acetonitrile (40 mL) was added triphenylphosphine (1.89 g, 7.228 mmol) at room temperature. The resulting reaction mixture was slowly heated to reflux overnight. The solvent was concentrated in vacuo and the residue was stirred with diisopropyl ether and filtered. The solid was dried under vacuum to afford 3.90 g of the product as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 1.17 (t, J=7.2 Hz, 3H), 4.08 (q, J=6.9 Hz, 2H), 5.35 (s, 1H), 5.40 (s, 1H), 7.20-7.22 (m, 1H), 7.37 (br s, 1H), 7.50 (d, J=4.5 Hz, 1H), 7.68-7.76 (m, 10H), 7.81-7.87 (m, 3H), 7.99 (d, J=3.9 Hz, 1H); ESI-MS (m/z) 471.24 (MH)+.