Water → HCID 69591877, compound

HRID 1827579Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)[CH:23]=2)[S:9]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])(=[O:11])=[O:10])=[CH:4][CH:3]=1.C[O:36][C:37](=[O:40])[CH:38]=[CH2:39].C(N(CC)CC)C.O>CN(C)C=O>[O:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH:29]1[O:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][N:8]([S:9]([C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[CH3:20])(=[O:11])=[O:10])[C:5]1[CH:4]=[CH:3][C:2]([CH:39]=[CH:38][C:37]([OH:40])=[O:36])=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of N-(4-iodo-phenyl)-2,4,6-trimethyl-N-[3-(tetrahydro-pyran-2yloxy)-benzyl]-benzenesulfonamide (1.06 g, 1.79 mmol) in dimethylformamide was added acrylic acid methyl ester (0.81 mL, 8.95 mmol), triethylamine (0.75 mL, 5.37 mmol), and palladium tetrakistriphenylphosphine (0.103 g, 0.09 mmol). The reaction mixture was stirred at 100° C. overnight. The reaction mixture was allowed to cool to room temperature and was poured into water. The reaction mixture was extracted with ethyl acetate and the organic layer was dried (magnesium sulfate) and concentrated. Medium pressure silica gel chromatography of the residue (1:1 hexanes:methylene chloride to methylene chloride to 20% ethyl acetate/methylene chloride) afforded 0.93 g (94%) of the title compound of Step A.

Workup

temperatureto cool to room temperature
extractionThe reaction mixture was extracted with ethyl acetate
dry with materialthe organic layer was dried (magnesium sulfate)
concentrationconcentrated

Sources & evidence

ORD record: ord-36a939518b8c46289cf6bc52c1c9a773
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07053212B2

Reaction notes

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