3-Fluoro-4-methoxyphenylboronic acid → HCID 18385612, compound

HRID 2298297Notes

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].[F:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]>>[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:24]2[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:22]([F:21])[CH:23]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

Reactant 2

HCID 27821943-Fluoro-4-methoxyphenylboronic acid

HCID 18385782HCID 18385782, compound

Product 1

HCID 18385612HCID 18385612, compoundYield 25.1%

Procedure

100 mg of 5-{4-(aminosulfonyl)phenyl}-2-ethyl-4-iodo-2-methyl-3(2H)-furanone was reacted with 80 mg of 3-fluoro-4-methoxybenzeneboronic acid by following a procedure similar to the procedure for the Step 2 of Example 35 to give 25 mg of 5-{4-(aminosulfonyl)phenyl}-2-ethyl-4-(3-fluoro-4-methoxyphenyl)-2-methyl-3(2H)-furanone as a solid. mp: 113-114° C. NMR: δ0.94 (t, J=7.5 Hz, 3H), 1.53 (s, 3H), 1.95 (q, J=7.5 Hz, 2H), 3.91 (s, 3H), 4.96 (br s, 2H), 6.99 (m, 3H), 7.80 (d, J=8.4 Hz, 2H), 7.93 (d, J=8.7 Hz, 2H). IR (cm−1): 3259, 1689, 1608, 1517, 1270, 1159. MS (FAB): 406 (m+1).

Sources & evidence

ORD record: ord-9c1af3dbcd414d9ebca544ea3bd3d53d
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492416B1

Reaction notes

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