Potassium Carbonate → HCID 71586283, compound

HRID 1465569Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[N:10]=[C:11]([NH:14][C:15](=[O:22])[C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[S:12][CH:13]=2)=[C:4]([CH3:23])[CH:3]=1.Br[C:25]1[CH:30]=[N:29][C:28]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu](I)I>[CH3:35][O:34][CH2:33][CH2:32][O:31][C:28]1[N:29]=[CH:30][C:25]([O:1][C:2]2[CH:3]=[C:4]([CH3:23])[C:5]([C:9]3[N:10]=[C:11]([NH:14][C:15](=[O:22])[C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)[S:12][CH:13]=3)=[C:6]([CH3:8])[CH:7]=2)=[N:26][CH:27]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-3 (0.50 g, 1.54 mmol), 2-bromo-5-(2-methoxyethoxy)pyrazine (22-2, 0.540 g, 2.32 mmol), copper iodide (15.0 mg, 0.080 mmol), and potassium carbonate (0.64 g, 4.63 mmol) in 3.1 mL of DMF was heated at 100° C. for 6.0 h. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (EtOAc:hexanes=5:1 as eluant) to give N-(4-(4-{(5-(2-methoxyethoxy)pyrazin-2-yl)oxy}-2,6-dimethylphenyl)thiazol-2-yl)isonicotinamide (22, 0.19 g) as brown solids: 1H NMR (500 MHz, CDCl3) δ 8.77 (d, J=4.5 Hz, 2 H), 7.91 (d, J=1.0 Hz, 1 H), 7.88 (d, J=1.0 Hz, 1 H), 7.73 (d, J=5.5 Hz, 2 H), 6.79 (s, 1 H), 6.63 (s, 2 H), 4.46 (t, J=4.5 Hz, 2 H), 3.75 (t, J=4.5 Hz, 2 H), 3.43 (s, 3 H), 1.98 (s, 6 H). ESI-MS: m/z 478.2 (M+H)+.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
custompurified by column chromatography on silica gel (EtOAc:hexanes=5:1 as eluant)

Sources & evidence

ORD record: ord-70a892ef00f3451a8dbdbf7add27d605
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999983B2

Reaction notes

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