Furan-3-boronic acid → (Z)-methyl 6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-3-(furan-3-yl)-2-hydroxybenzoate

HRID 2177841Notes

Reaction equation

HRID 2177841 reaction equation
[CH2:1]([N:3]([CH2:35][CH3:36])[CH2:4]/[CH:5]=[CH:6]\[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([CH2:17][C:18]1[C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]([O:28]C)[C:21]([C:30]2[CH:34]=[CH:33][O:32][CH:31]=2)=[CH:20][CH:19]=1)(=[O:16])=[O:15])[CH3:2].BrC1C(O)=C(C(CS(C2C=CC(F)=CC=2/C=C\CN(CC)CC)(=O)=O)=CC=1)C(OC)=O.O1C=CC(B(O)O)=C1>>[CH2:35]([N:3]([CH2:1][CH3:2])[CH2:4]/[CH:5]=[CH:6]\[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([CH2:17][C:18]1[C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]([OH:28])[C:21]([C:30]2[CH:34]=[CH:33][O:32][CH:31]=2)=[CH:20][CH:19]=1)(=[O:15])=[O:16])[CH3:36]

Participants

4

Reactant 3

HCID 2734358Furan-3-boronic acidHCID 66693503(Z)-methyl 3-bromo-6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-2-hydroxybenzoate2×HCID 69915014(Z)-methyl 6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-3-(furan-3-yl)-2-methoxybenzoate

Product 1

HCID 86677120(Z)-methyl 6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-3-(furan-3-yl)-2-hydroxybenzoate

Procedure

Prepared by proceeding in a similar manner to Intermediate 160, starting from (Z)-methyl 3-bromo-6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-2-hydroxybenzoate (Intermediate 197) and furan-3-boronic acid.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-dc9cbbdf33274665a329441a29bb17b4
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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