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

HRID 1882137Notes

Reaction equation

HRID 1882137 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][CH:42]([F:44])[F:43])=[CH:39][CH:38]=[CH:37][C:34]=2[CH:35]=O)[CH2:31][CH2:30][CH2:29][CH2:28]1.[Br-].[CH2:46]([O:48][C:49]([C:51]1[N:58]2[C:54]([S:55][CH:56]=[CH:57]2)=[N:53][C:52]=1[CH2:59][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:50])[CH3:47].[H-].[Na+]>CS(C)=O>[CH:27]1([O:32][C:33]2[C:40]([O:41][CH:42]([F:44])[F:43])=[CH:39][CH:38]=[CH:37][C:34]=2/[CH:35]=[CH:59]/[C:52]2[N:53]=[C:54]3[N:58]([C:51]=2[C:49]([O:48][CH2:46][CH3:47])=[O:50])[CH:57]=[CH:56][S:55]3)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 593698916-{(E)-2-[2-(Cyclopropylmethoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acidHCID 593698942-(Cyclopentyloxy)-3-(difluoromethoxy)benzaldehydeHCID 866425275-Ethyloxy carbonylimidazo[2,1-b][1,3]thiazol-6-yl-methyl(triphenyl)phosphonium bromide

Product 1

HCID 67549214Ethyl 6-{(E)-2-[2-(cyclopentyloxy)-3-(difluoromethoxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylateYield 80.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This compound was prepared as described in Intermediate 1, step-4, by the reaction of 2-(cyclopentyloxy)-3-(difluoromethoxy)benzaldehyde (3.26 g, 12.766 mmol) with 5-ethyloxy carbonylimidazo[2,1-b][1,3]thiazol-6-yl-methyl(triphenyl)phosphonium bromide (6.40 g, 11.605 mmol) in the presence of sodium hydride (510 mg, 12.766 mmol) in anhydrous DMSO (20 mL) to give 4.20 g the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.40 (t, J=6.9 Hz, 3H), 1.54-1.60 (m, 2H), 1.65-1.72 (m, 2H), 1.80-1.86 (m, 4H), 4.35-4.44 (m, 2H), 4.70-4.78 (m, 1H), 7.10-7.16 (m, 2H), 7.18 (t, J=73.2 Hz, 1H), 7.40-7.46 (m, 1H), 7.54-7.60 (m, 1H), 7.74 (d, J=15.9 Hz, 1H), 7.85 (d, J=16.2 Hz, 1H), 8.10-8.16 (m, 1H); ESI-MS (m/z) 449.10 (M+H)+.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-434a97dbcf944dc090e9536bdba25180
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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