Furan-3-boronic acid → Methyl 3-(furan-3-yl)-6-((2-(3-hydroxyprop-1-enyl)benzenesulfonyl)methyl)-2-methoxybenzoate

HRID 2177721Notes

Reaction equation

HRID 2177721 reaction equation
C1(S(CC2C=[CH:19][C:18]([C:21]3[O:25][CH:24]=NC=3)=CC=2C(OC)=O)(=O)=O)C=CC=CC=1.Br[C:27]1[C:28]([O:51][CH3:52])=[C:29]([C:34]([CH2:37][S:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[CH:47]=[CH:48][CH2:49][OH:50])(=[O:40])=[O:39])=[CH:35][CH:36]=1)[C:30]([O:32][CH3:33])=[O:31].C1(S(CC2C(C(OCC)=O)=C(OC)C(Br)=CC=2)(=O)=O)C=CC=CC=1.O1C=CC(B(O)O)=C1>>[O:25]1[CH:21]=[CH:18][C:19]([C:27]2[C:28]([O:51][CH3:52])=[C:29]([C:34]([CH2:37][S:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[CH:47]=[CH:48][CH2:49][OH:50])(=[O:39])=[O:40])=[CH:35][CH:36]=2)[C:30]([O:32][CH3:33])=[O:31])=[CH:24]1

Participants

5

Reactant 4

HCID 2734358Furan-3-boronic acidHCID 67107394Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoateHCID 67107594Methyl 2-(benzenesulphonylmethyl)-5-(oxazol-5-yl)benzoateHCID 67107632Methyl 3-bromo-6-((2-(3-hydroxyprop-1-enyl)benzenesulfonyl)methyl)-2-methoxybenzoate

Product 1

HCID 67107768Methyl 3-(furan-3-yl)-6-((2-(3-hydroxyprop-1-enyl)benzenesulfonyl)methyl)-2-methoxybenzoate

Procedure

Prepared by proceeding in a similar manner to Intermediate 42, starting from methyl 3-bromo-6-((2-(3-hydroxyprop-1-enyl)benzenesulfonyl)methyl)-2-methoxybenzoate (mixture of E and Z isomers, Intermediate 60) and furan-3-yl boronic acid.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-948889b4d37944fe8b0968f8980ba0aa
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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