Phenylboronic Acid → HCID 18385854, compound

HRID 2298296Notes

Reaction equation

[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([CH2:17][CH3:18])([CH3:16])[C:13](=[O:19])[C:12]=2I)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([CH2:17][CH3:18])([CH3:16])[C:13](=[O:19])[C:12]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

Reactant 2

HCID 66827Phenylboronic Acid

HCID 18385782HCID 18385782, compound

Product 1

HCID 18385854HCID 18385854, compoundYield 34.2%

Procedure

100 mg of 5-{4-(aminosulfonyl)phenyl}-2-ethyl-4-iodo-2-methyl-3(2H)-furanone was reacted with 90 mg of benzeneboronic acid by following a procedure similar to Step 2 of Example 35 to give 30 mg of 5-{4-(aminosulfonyl)phenyl}-2-ethyl-2-methyl-4-phenyl-3(2H)-furanone as a solid. mp: 153-154° C. NMR: δ0.95 (t, J=7.5 Hz, 3H), 1.54 (s, 3H), 1.97 (m, 2H), 4.89 (br s, 2H), 7.26 (m, 2H), 7.36 (m, 3H), 7.79 (d, J=8.7 Hz, 2H), 7.90 (d, J=8.7 Hz, 2H). IR (cm−1): 3340, 3256, 1684, 1616, 1392, 1342, 1161.

Sources & evidence

ORD record: ord-f04ff14a1842481d86764fe977b7a205
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492416B1

Reaction notes

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