HCID 21099516, compound → HCID 21099397, compound

HRID 2376969Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:12]=[CH:13][C:14]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[C:15]([CH:18]=1)[CH:16]=[O:17].[CH3:28][Mg]Cl>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:12]=[CH:13][C:14]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[C:15]([CH:16]([OH:17])[CH3:28])[CH:18]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 5-[(E)-2-(2,4-difluorophenyl)vinyl]-2-(phenylsulfonyl)benzaldehyde (prepared from Example 58 according to the method of Example 50 Step 1, 74 mg, 0.193 mmol) in tetrahydrofuran (2 mL) was cooled to −78° C. under nitrogen. Methylmagnesium chloride (3.0M in tetrahydrofuran, 0.15 mL, 0.424 mmol) was added and the reaction stirred for 30 minutes then quenched with 1N HCl (5 mL) and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 30% ethyl acetate/isohexane to obtain the title compound as a white solid (56 mg, 72%). δH (360 MHz, d6 DMSO): 8.02 (1H, d, J=8.3 Hz), 7.95-7.59 (8H, m), 7.39 (2H, s), 7.33-7.27 (1H, m), 7.14 (1H, td, J=2.1, 8.5 Hz), 5.37 (2H, t, J=5.4 Hz), 1.07 (3H, d, J=5.9 Hz).

Workup

customthen quenched with 1N HCl (5 mL)
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over MgSO4
customevaporated in vacuo
customThe residue was purified by flash column chromatography on silica
washeluting with 30% ethyl acetate/isohexane

Sources & evidence

ORD record: ord-137b11f155714617bec2e1a9bdfa0195
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468393B2

Reaction notes

Loading…