Benzo[b]furan-2-boronic acid → HCID 18385997, compound

HRID 2298285Notes

Reaction equation

[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13](=[O:18])[C:12]=2I)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[O:20]1[C:24](B(O)O)=[CH:23][C:22]2[CH:28]=[CH:29][CH:30]=[CH:31][C:21]1=2>>[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13](=[O:18])[C:12]=2[C:24]2[O:20][C:21]3[CH:31]=[CH:30][CH:29]=[CH:28][C:22]=3[CH:23]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

Reactant 2

HCID 2776266Benzo[b]furan-2-boronic acid

HCID 18385833HCID 18385833, compound

Product 1

HCID 18385997HCID 18385997, compoundYield 23.1%

Procedure

200 mg of 5-{4-(aminosulfonyl)phenyl}-2,2-dimethyl-4-iodo-3(2H)-furanone was coupled with 99 mg of benzo[b]furan-2-boronic acid by following a procedure similar to Step 4 of Example 22 to give 45 mg of 5-{4-(aminosulfonyl)phenyl}-4-(2-benzo[b]furanyl)-2,2-dimethyl-3(2H)-furanone as a solid. mp: 143-145° C. NMR: δ1.60 (s, 6H), 4.92 (br s, 2H), 7.23 (m, 3H), 7.72 (m, 2H), 8.02 (m, 4H), IR (cm−1): 3384, 3245, 1698, 1510, 1253, 1161, 793.

Sources & evidence

ORD record: ord-99740b682ce0410e8d95541add6c2af0
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492416B1

Reaction notes

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