Furan-2-boronic acid → HCID 18386037, compound

HRID 2298319Notes

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].[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1B(O)O>>[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:22]2[O:21][CH:25]=[CH:24][CH:23]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

Reactant 2

HCID 2734357Furan-2-boronic acid

HCID 18385782HCID 18385782, compound

Product 1

HCID 18386037HCID 18386037, compound

Procedure

5-{4-(Aminosulfonyl)phenyl}-2-ethyl-4-iodo-2-methyl-3(2H)-furanone was coupled with 2-furanboronic acid according to a procedure similar to the procedure in Example 44. mp: 154-155° C. NMR: δ0.92 (t, J=7.5 Hz, 3H), 1.52 (s, 3H), 1.95 (m, 2H), 5.03 (br s, 2H), 6.51 (dd, J=3.0, 1.8 Hz, 1H), 6.87 (d, J=3.0 Hz, 2H), 7.37 (d, J=1.5Hz, 1H), 7.94 (d, J=8.7 Hz, 2H), 8.02 (d, J=8.7 Hz, 2H). IR (cm−1): 3347, 3257, 1692, 1545, 1341, 1164.

Sources & evidence

ORD record: ord-a0a41ab2739746afb7254d1922cf47fc
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492416B1

Reaction notes

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