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

HRID 1882136Notes

Reaction equation

HRID 1882136 reaction equation
C1(COC2C(OC)=CC=CC=2/C=C/C2N=C3N(C=2C(O)=O)C=CS3)CC1.[CH:27]1([O:32][C:33]2[C:40]([O:41][CH3:42])=[CH:39][CH:38]=[CH:37][C:34]=2[CH:35]=O)[CH2:31][CH2:30][CH2:29][CH2:28]1.[Br-].[CH2:44]([O:46][C:47]([C:49]1[N:56]2[C:52]([S:53][CH:54]=[CH:55]2)=[N:51][C:50]=1[CH2:57][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:48])[CH3:45].[H-].[Na+]>CS(C)=O>[CH:27]1([O:32][C:33]2[C:40]([O:41][CH3:42])=[CH:39][CH:38]=[CH:37][C:34]=2/[CH:35]=[CH:57]/[C:50]2[N:51]=[C:52]3[N:56]([C:49]=2[C:47]([O:46][CH2:44][CH3:45])=[O:48])[CH:55]=[CH:54][S:53]3)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 6484666HCID 6484666, compoundHCID 593698916-{(E)-2-[2-(Cyclopropylmethoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acidHCID 866425275-Ethyloxy carbonylimidazo[2,1-b][1,3]thiazol-6-yl-methyl(triphenyl)phosphonium bromide

Product 1

HCID 67548575Ethyl 6-{(E)-2-[2-(cyclopentyloxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylateYield 71.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This compound was prepared as described in Intermediate 1 by the reaction of 2-(cyclopentyloxy)-3-methoxybenzaldehyde (1.318 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 (239 mg, 5.984 mmol) in anhydrous DMSO (20 mL) to give 1.610 g of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.40 (t, J=6.9 Hz, 3H), 1.54-1.65 (m, 4H), 1.78-1.85 (m, 4H), 3.81 (s, 3H), 4.39 (q, J=7.2 Hz, 2H), 4.83-4.86 (m, 1H), 6.99-7.02 (m, 1H), 7.09 (t, J=8.1 Hz, 1H), 7.21-7.25 (m, 1H), 7.46 (d, J=4.5 Hz, 1H), 7.67 (d, J=16.2 Hz, 1H), 7.88 (d, J=16.2 Hz, 1H), 8.12 (d, J=4.5 Hz, 1H); ESI-MS (m/z) 413.27 (M+H)+.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-e9fb00ccad50420c9f7ec1e251d70147
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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