1-Bromo-3-methylbutane → Ethyl 2-{(E)-2-[3-(Difluoromethoxy)-2-(3-methylbutoxy)phenyl]vinyl}imidazo[1,2-a]pyridine-3-carboxylate

HRID 1882146Notes

Reaction equation

HRID 1882146 reaction equation
[F:1][CH:2]([F:27])[O:3][C:4]1[C:5]([OH:26])=[C:6](/[CH:10]=[CH:11]/[C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]3[C:20]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:7]=[CH:8][CH:9]=1.Br[CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32].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:27][CH:2]([F:1])[O:3][C:4]1[C:5]([O:26][CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[C:6](/[CH:10]=[CH:11]/[C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]3[C:20]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 78911-Bromo-3-methylbutaneHCID 11430Potassium CarbonateHCID 59369912Ethyl 2-{(E)-2-[3-(difluoromethoxy)-2-hydroxyphenyl]vinyl}imidazo[1,2-a]pyridine-3-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 86761713Ethyl 2-{(E)-2-[3-(Difluoromethoxy)-2-(3-methylbutoxy)phenyl]vinyl}imidazo[1,2-a]pyridine-3-carboxylateYield 101%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Alkylation of Intermediate 12 (400 mg, 1.069 mmol) with 1-bromo-3-methylbutane (193.8 mg, 1.283 mmol) in presence of potassium carbonate (163 mg, 1.175 mmol) in anhydrous N,N-dimethylformamide (4 mL) as described in Intermediate 7A, Step 1 gave 480 mg of the compound as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.94 (d, J=6.9, 6H), 1.40-1.47 (m, 3H), 1.64-1.71 (m, 2H), 1.88-1.95 (m, 1H), 3.97-4.03 (m, 2H), 4.40-4.48 (m, 2H), 7.12-7.20 (m, 2H), 7.21 (t, J=74.7 Hz, 1H), 7.22-7.28 (m, 1H), 7.53-7.62 (m, 2H), 7.74 (d, J=8.4 Hz, 1H), 7.94 (d, J=15.9 Hz, 1H), 8.04 (d, J=16.2 Hz, 1H), 9.23 (d, J=6.3 Hz, 1H); ESI-MS (m/z) 445.25 (M)+.

Sources & evidence

ORD record
ord-545ad4eb071e480e93b0e8821c3f8eac
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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