Sodium hydride → Ethyl 6-{(E)-2-[2-(isobutoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylate
Reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=2/[CH:14]=[CH:15]/[C:16]2[N:17]=[C:18]3[N:22]([C:23]=2[C:24]([OH:26])=[O:25])[CH:21]=[CH:20][S:19]3)[CH2:3][CH2:2]1.[CH2:27](OC1C(OC)=CC=CC=1C=O)[CH:28](C)C.[Br-].C(OC(C1N2C(SC=C2)=NC=1C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)C.[H-].[Na+]>CS(C)=O>[CH2:4]([O:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1/[CH:14]=[CH:15]/[C:16]1[N:17]=[C:18]2[N:22]([C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:21]=[CH:20][S:19]2)[CH:1]([CH3:2])[CH3:3]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
This compound was prepared as described in Intermediate 1 by the reaction of 2-isobutoxy-3-methoxybenzaldehyde (1.328 g, 5.984 mmol) with 5-ethyloxycarbonylimidazo[2,1-b][1,3]thiazol-6-yl-methyl(triphenyl)phosphonium bromide (3.0 g, 5.440 mmol) in the presence of sodium hydride (0.23 g, 5.984 mmol) in anhydrous DMSO (15 mL) to give 1.50 g of product as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.07 (d, J=6.9 Hz, 6H), 1.47 (t, J=6.9 Hz, 3H), 2.12-2.23 (m, 1H), 3.75 (d, J=6.6 Hz, 2H), 3.86 (s, 3H), 4.40-4.49 (m, 2H), 6.85 (d, J=7.8 Hz, 1H), 6.90 (d, J=4.5 Hz, 1H), 7.05 (t, J=7.8 Hz, 1H), 7.28-7.33 (m, 1H), 7.76 (d, J=16.2 Hz, 1H), 8.03 (d, J=16.2 Hz, 1H), 8.07-8.11 (m, 1H); APCI-MS (m/z) 399.09 (M−H)−.
Workup
- customThis compound was prepared
Sources & evidence
- ORD record
- ord-d5ddf50ded68477981a29ea05b4a0c3a
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318928B2
Reaction notes
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