Tetrahydrofuran → HCID 178491267, compound

HRID 877386Notes

Reaction equation

[CH3:1][C:2]([S:5](/[N:7]=[CH:8]/[C:9]1[N:10]=[C:11]([CH3:14])[NH:12][CH:13]=1)=[O:6])([CH3:4])[CH3:3].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([Mg]Br)=[CH:19][CH:18]=1.C1COCC1>C(Cl)Cl>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:8]([C:9]2[N:10]=[C:11]([CH3:14])[NH:12][CH:13]=2)[NH:7][S:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])=[CH:19][CH:18]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a 100 ml round bottom flask containing −78° C. solution of 2-methyl-N-((1E)-(2-methyl-1H-imidazol-4-yl)methylene]propane-2-sulfinamide (1.170 g, 5.490 mmol) in 25.0 ml of CH2Cl2 was added dropwise 1.0 N 4-methoxyphenylmagnesium bromide in THF (8.230 ml, 8.230 mmol). The resulting solution was stirred at −78° C. for 1 hour. The reaction mixture was quenched with saturated NH4Cl and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuum. Purification by flash chromatography (SiO2, 0-4% methanol in CH2Cl2, gradient) gave the title compound as a white solid (0.735 g, 42%). 1H NMR (CDCl3, 400 MHz) δ 7.270 (m, 2H), 6.849 (m, 2H), 6.405 (s, 1H), 5.451 (d, J=6.04 Hz, 1H), 4.307 (d, J=6.05 Hz, 1H), 3.791 (s, 3H), 3.433 (s, 1H), 2.282 (s, 3H), 1.251 (s, 9H). ES-MS [M+1]+: 322.3.

Workup

customThe reaction mixture was quenched with saturated NH4Cl
extractionextracted with CH2Cl2
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationThe filtrate was concentrated in vacuum
customPurification by flash chromatography (SiO2, 0-4% methanol in CH2Cl2, gradient)

Sources & evidence

ORD record: ord-3c732dac434c4b7e88bce4435179d9f5
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987310B2

Reaction notes

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