2-[2-(Tert-butyldimethylsilanyloxy)-ethyl]-furan-3-yl-boronic acid → Methyl 6-amino-3-{2-[2-(tert-butyldimethylsilanyloxy)-ethyl]-furan-3-yl}-2-hydroxybenzoate

HRID 1778356Notes

Reaction equation

HRID 1778356 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([OH:12])[C:5](Br)=[CH:4][CH:3]=1.[Si:14]([O:21][CH2:22][CH2:23][C:24]1[O:25][CH:26]=[CH:27][C:28]=1B(O)O)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>>[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([OH:12])[C:5]([C:28]2[CH:27]=[CH:26][O:25][C:24]=2[CH2:23][CH2:22][O:21][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 666857952-[2-(Tert-butyldimethylsilanyloxy)-ethyl]-furan-3-yl-boronic acid2×HCID 66685945Methyl 6-amino-3-bromo-2-hydroxybenzoate

Product 1

HCID 86684732Methyl 6-amino-3-{2-[2-(tert-butyldimethylsilanyloxy)-ethyl]-furan-3-yl}-2-hydroxybenzoate

Procedure

Prepared by proceeding in a similar manner to Intermediate 26, starting from methyl 6-amino-3-bromo-2-hydroxybenzoate (prepared according to Wang et al, Bioorg Med Chem Lett 2007 17 2817) and 2-[2-(tert-butyldimethylsilanyloxy)-ethyl]-furan-3-yl-boronic acid (Intermediate 33). The material was used without further characterisation.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0ae4ed4858aa4f63a751a16a8362b829
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

Loading…