1-Bromo-3-methylbutane → Ethyl 6-{(E)-2-[3-(difluoromethoxy)-2-(3-methylbutoxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylate

HRID 1882140Notes

Reaction equation

HRID 1882140 reaction equation
[F:1][CH:2]([F:26])[O:3][C:4]1[C:5]([OH:25])=[C:6](/[CH:10]=[CH:11]/[C:12]2[N:13]=[C:14]3[N:18]([C:19]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:17]=[CH:16][S:15]3)[CH:7]=[CH:8][CH:9]=1.Br[CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31].C(=O)([O-])[O-].[K+].[K+].FC(F)OC1C(OCC(C)(C)C)=C(/C=C/C2N=C3N(C=2C(O)=O)C=CS3)C=CC=1>CN(C)C=O>[F:26][CH:2]([F:1])[O:3][C:4]1[C:5]([O:25][CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])=[C:6](/[CH:10]=[CH:11]/[C:12]2[N:13]=[C:14]3[N:18]([C:19]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:17]=[CH:16][S:15]3)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 78911-Bromo-3-methylbutaneHCID 11430Potassium CarbonateHCID 59369921Ethyl 6-{(E)-2-[3-(difluoromethoxy)-2-hydroxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylateHCID 684073456-{(E)-2-[3-(Difluoromethoxy)-2-(2,2-dimethylpropoxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid

Product 1

HCID 68406133Ethyl 6-{(E)-2-[3-(difluoromethoxy)-2-(3-methylbutoxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylateYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Alkylation of Intermediate 6 (400 mg, 1.052 mmol) with 1-bromo-3-methylbutane (159 mg, 1.262 mmol) in presence of potassium carbonate (159 mg, 1.157 mmol) in anhydrous N,N-dimethylformamide (4 mL) as described in Intermediate 7A gave 475 mg of the compound as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.93 (t, J=6.6 Hz, 6H), 1.40 (t, J=7.2 Hz, 3H), 1.66 (q, J=6.3 Hz, 2H), 1.82-1.90 (m, 1H), 3.96 (t, J=6.3 Hz, 2H), 4.40 (q, J=6.9 Hz, 2H), 7.19 (t, J=71.4 Hz, 1H), 7.20-7.28 (m, 2H), 7.42-7.50 (m, 1H), 7.53-7.60 (m, 1H), 7.80 (s, 2H), 8.13 (d, J=4.2 Hz, 1H); APCI-MS (m/z) 451.23 (M+H)+.

Sources & evidence

ORD record
ord-d1c76280494749b58663c12cb7f5ccda
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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