Dimethyl Disulfide → HCID 135461995, compound

HRID 2053446Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]1[O:17][N:16]=[C:15]([CH3:18])[CH:14]=1)=[C:5]2[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([Mg]Cl)(C)C.[Li]CCCC.[CH3:35][S:36]SC>C1COCC1>[CH3:18][C:15]1[CH:14]=[C:13]([C:6]2[C:7](=[O:12])[NH:8][C:9]3[C:4]([C:5]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:3][C:2]([S:36][CH3:35])=[CH:11][CH:10]=3)[O:17][N:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A flask was charged with 6-bromo-3-(3-methyl-isoxazol-5-yl)-4-phenyl-1H-quinolin-2-one (30 mg, 0.079 mmol)(example 39), 1 mL of THF and cooled to 0° C. A 2M solution of i-PrMgCl in THF (0.39 mL, 0.077 mmol) was added and the reaction stirred for 5 minutes at 0° C. and then cooled to −78° C. and a 2M solution of n-BuLi in hexanes (0.06 mL, 0.12 mmol) was added. After stirring for 15 minutes dimethyldisulfide (15 mg, 0.16 mmol) was added and the reaction allowed to attain RT and stirred for 30 minutes. The reaction was diluted with EtAc (10 mL) and washed with brine (2×10 mL). The organic layer was concentrated and the title product (14 mg, 50%) eluted from a 5 g SPE with 50% EtOAc/hexanes. 1H NMR (400 MHz, CD3OD) δ 7.54 (dd, 1H), 7.48 (m, 3H), 7.48 (d, 1H), 7.24 (m, 2H), 7.06 (d, 1H), 6.36 (s, 1H), 2.34 (s,3H), 2.24 (s, 3H). Mass spectrum (ESI, m/z) calcd. for C20H16N2O2S 348.1, found 349.1 (M+H).

Workup

temperaturecooled to −78° C.
additionwas added
customto attain RT
stirringstirred for 30 minutes
additionThe reaction was diluted with EtAc (10 mL)
washwashed with brine (2×10 mL)
concentrationThe organic layer was concentrated
washthe title product (14 mg, 50%) eluted from a 5 g SPE with 50% EtOAc/hexanes

Sources & evidence

ORD record: ord-8cc62cc79fb14e2da91a404df1fa7ad4
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07326788B2

Reaction notes

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