(2H-1,3-benzodioxol-5-yl)boronic acid → HCID 18386024, compound

HRID 2298284Notes

Reaction equation

HRID 2298284 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].[CH2:20]1[O:28][C:27]2[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][C:22]=2[O:21]1>>[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:25]2[CH:24]=[CH:23][C:22]3[O:21][CH2:20][O:28][C:27]=3[CH:26]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

3

Reactant 2

HCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 18385833HCID 18385833, compound

Product 1

HCID 18386024HCID 18386024, compoundYield 33.8%

Procedure

120 mg of 5-{4-(aminosulfonyl)phenyl}-2,2-dimethyl-4-iodo-3(2H)-furanone was reacted with 100 mg of 3,4-(methylenedioxy)benzeneboronic acid by following a procedure similar to Step 4 of Example 22 to yield 40 mg of 5-{4-(aminosulfonyl)phenyl}-2,2-dimethyl-4-{3,4-(methylenedioxy)phenyl}-3(2H)-furanone as a solid. mp: 178-179° C. NMR: δ1.56 (s, 6H), 4.89 (br s, 2H), 5.99 (s, 2H), 6.74 (m, 2H), 6.83 (m, 1H), 7.82 (d, J=9.0 Hz, 2H), 7.92 (d, J=9.0 Hz, 2H). IR (cm−1): 3237, 1682, 1338, 1245, 1164.

Sources & evidence

ORD record
ord-cdf0bc38ecd94801aa0696c3182de818
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

Loading…