trans-2-(4-Chlorophenyl)vinylboronic acid → methyl 6-[({2-[(E)-2-(4-chlorophenyl)vinyl]phenyl}sulfonyl)amino]-3-ethyl-2-methoxybenzoate

HRID 1726015Notes

Reaction equation

HRID 1726015 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([O:22][CH3:23])[C:15]([CH2:24][CH3:25])=[CH:14][CH:13]=1)(=[O:10])=[O:9].[Cl:26][C:27]1[CH:32]=[CH:31][C:30](/[CH:33]=[CH:34]/B(O)O)=[CH:29][CH:28]=1>>[Cl:26][C:27]1[CH:32]=[CH:31][C:30](/[CH:33]=[CH:34]/[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8]([NH:11][C:12]2[C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([O:22][CH3:23])[C:15]([CH2:24][CH3:25])=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 642694trans-2-(4-Chlorophenyl)vinylboronic acidHCID 68865762Methyl 6-{[(2-bromophenyl)sulfonyl]amino}-3-ethyl-2-methoxybenzoate

Product 1

HCID 68863661methyl 6-[({2-[(E)-2-(4-chlorophenyl)vinyl]phenyl}sulfonyl)amino]-3-ethyl-2-methoxybenzoate

Procedure

The title compound-was prepared from Example 574D (0.215 g, 0.5 mmol) and trans-2-(4-chlorophenyl)vinyl boronic acid according to the procedure of Example 230B, yielding 0.252 g, 100%. 1H NMR (DMSO-d6) δ 1.02 (t, 3H), 2.42 (q, 2H), 3.52 (s, 3H), 3.54 (s, 3H), 6.90 (d, 1H), 7.16 (d, 1H), 7.22 (d, 1H), 7.40-7.70 (m, 7H), 7.80 (d, 1H), 7.90 (d, 1H), 10.00 (s, 1H); MS (ESI(−)) m/e 484 (M−H)−.

Sources & evidence

ORD record
ord-0710915b06544a5da8deebcb39dbde9a
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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