Pyridine → methyl(5-{3-[4-(4-ethyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy}-1H-indol-1-yl)acetate

HRID 2424963Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:31])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([NH2:27])=[S:26])=[CH:21][C:20]=3[CH2:28][CH2:29][CH3:30])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.Br[CH2:33][C:34](=O)[CH2:35][CH3:36].N1C=CC=CC=1>C(O)C>[CH3:1][O:2][C:3](=[O:31])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[S:26][CH:33]=[C:34]([CH2:35][CH3:36])[N:27]=4)=[CH:21][C:20]=3[CH2:28][CH2:29][CH3:30])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl(5-{3-[4-(aminocarbonothioyl)-2-propyl-phenoxy]-propoxy}-1H-indol-1-yl)acetate (Example 52, 500 mg, 1.14 mmol) in ethanol (35 mL), was added 1-bromo-2-butanone (739 mg, 2.27 mmol) and pyridine (0.14 mL, 135 mg, 1.70 mmol). The reaction mixture was stirred for 3 h at 70° C. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (0-15% EtOAc in hexane) to give 89 mg (16%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.75-7.70 (m, 2H), 7.18-7.12 (m, 2H), 7.05 (d, 1H) 6.95-6.85 (m, 2H), 6.80 (s, 1H), 6.48 (d, 1H), 4.85 (s, 2H), 4.25-4.20 (m, 4H), 3.75 (s, 3H), 2.85 (q, 2H), 2.70-2.60 (m, 2H), 2.40-2.30 (m, 2H), 1.75-1.60 (m, 2H), 1.35 (t, 3H), 0.95 (t, 3H).

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel chromatography (0-15% EtOAc in hexane)

Sources & evidence

ORD record: ord-2f9f5c03b14f4fa382714ebd6f06e56a
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964622B2

Reaction notes

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