Ethyl Acetate → HCID 87616494, compound

HRID 735353Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18]([C:21]2[N:28]=[CH:27][CH:26]=[CH:25][C:22]=2[CH:23]=O)(=[O:20])=[O:19])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1.[CH3:29][C:30]([S:33]([NH2:35])=[O:34])([CH3:32])[CH3:31].C(OCC)(=O)C>C1COCC1.[Cl-].[Na+].O.[O-]CC.[O-]CC.[O-]CC.[O-]CC.[Ti+4]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18]([C:21]2[C:22](/[CH:23]=[N:35]/[S:33]([C:30]([CH3:32])([CH3:31])[CH3:29])=[O:34])=[CH:25][CH:26]=[CH:27][N:28]=2)(=[O:20])=[O:19])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}nicotinaldehyde (300 mg, 0.77 mmol) in THF (1.6 mL) was added 2-methylpropane-2-sulfinamide (102 mg, 0.84 mmol) and titanium tetraethoxide (0.32 mL, 1.54 mmol). The reaction was heated for 8 hours at 80° C. The reaction mixture was poured into brine, ethyl acetate was added and the mixture stirred for 10 minutes. The organic layer was separated and washed with water and brine, filtered through Hyflo and the volatiles evaporated in vacuo to give the title compound as solid (170 mg). 1H NMR (400 MHz, d6-DMSO): δ 9.60 (1H, s), 8.75 (1H, s), 8.72 (1H, d, J=4.6 Hz), 8.57 (1H, d, J=7.9 Hz), 8.40 (1H, s), 8.34 (1H, d, J=8.7 Hz), 8.24 (1H, d, J=8.7 Hz), 8.05 (1H, d, J=7.5 Hz), 7.93 (3H, dd, J=6.3, 8.5 Hz), 7.82 (1H, dd, J=4.6, 7.9 Hz), 7.39 (2H, t, J=8.8 Hz), 1.24 (9H, s).

Workup

additionwas added
customThe organic layer was separated
washwashed with water and brine
filtrationfiltered through Hyflo
customthe volatiles evaporated in vacuo

Sources & evidence

ORD record: ord-182c80f2759b45fa8843b30a244d9b79
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592456B2

Reaction notes

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