Sodium hydride → Ethyl 6-{(e)-2-[2-(cyclopropylmethoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylate

HRID 1882131Notes

Reaction equation

HRID 1882131 reaction equation
[Br-].[CH2:2]([O:4][C:5]([C:7]1[N:14]2[C:10]([S:11][CH:12]=[CH:13]2)=[N:9][C:8]=1[CH2:15][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:6])[CH3:3].[H-].[Na+].[CH:37]1([CH2:40][O:41][C:42]2[C:49]([O:50][CH3:51])=[CH:48][CH:47]=[CH:46][C:43]=2[CH:44]=O)[CH2:39][CH2:38]1>CS(C)=O.C(OCC)(=O)C>[CH:37]1([CH2:40][O:41][C:42]2[C:49]([O:50][CH3:51])=[CH:48][CH:47]=[CH:46][C:43]=2/[CH:44]=[CH:15]/[C:8]2[N:9]=[C:10]3[N:14]([C:7]=2[C:5]([O:4][CH2:2][CH3:3])=[O:6])[CH:13]=[CH:12][S:11]3)[CH2:38][CH2:39]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 435604072-(Cyclopropylmethoxy)-3-methoxybenzaldehydeHCID 866425275-Ethyloxy carbonylimidazo[2,1-b][1,3]thiazol-6-yl-methyl(triphenyl)phosphonium bromide

Product 1

HCID 67549791Ethyl 6-{(e)-2-[2-(cyclopropylmethoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of Step 3 intermediate (2.0 g, 3.626 mmol) was added NaH (0.160 g, 3.989 mmol) in anhydrous DMSO (10 mL) and stirred for 30 min. A solution of 2-(cyclopropylmethoxy)-3-methoxybenzaldehyde (0.82 g, 3.989 mmol) in anhydrous DMSO (10 mL) was added drop wise to this solution at room temperature and stirred for 2 h. The reaction mixture was diluted with ethyl acetate (200 mL), washed with water (2×50 mL), brine and dried (Na2SO4) to yield a crude solid which was purified by column chromatography using 5% ethyl acetate in petroleum ether to afford 0.776 g of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.26-0.28 (m, 2H), 0.50-0.53 (m, 2H), 1.17-1.23 (m, 1H), 1.39 (t, J=7.5 Hz, 3H), 3.75 (d, J=7.2 Hz, 2H), 3.79 (s, 3H), 4.37 (q, J=6.9 Hz, 2H), 6.95-6.99 (m, 2H), 7.08 (t, J=7.8 Hz, 1H), 7.18-7.22 (m, 1H), 7.43 (d, J=4.5 Hz, 1H), 7.69 (d, J=16.2 Hz, 1H), 7.92 (d, J=16.5 Hz, 1H), 8.10 (d, J=4.2 Hz, 1H); ESI-MS (m/z) 399.20 (MH)+.

Workup

  1. stirringstirred for 2 h
  2. washwashed with water (2×50 mL), brine
  3. dry with materialdried (Na2SO4)
  4. customto yield a crude solid which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-d856ab59165445268c8d395747e56718
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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