(E)-4-(methylsulfonamido) styrylboronic acid → (E)-N-(4-(3-tert-butyl-5-(2,4-di-tert-butoxypyrimidin-5-yl)-2-methoxystyryl)phenyl)methanesulfonamide

HRID 403668Notes

Reaction equation

HRID 403668 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:14]2[C:15]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[N:16][C:17]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[N:18][CH:19]=2)[CH:5]=[C:6]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:7]=1[O:8][CH3:9].[CH3:30][S:31]([NH:34][C:35]1[CH:45]=[CH:44][C:38](/[CH:39]=[CH:40]/B(O)O)=[CH:37][CH:36]=1)(=[O:33])=[O:32]>>[C:10]([C:6]1[C:7]([O:8][CH3:9])=[C:2]([CH:3]=[C:4]([C:14]2[C:15]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[N:16][C:17]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[N:18][CH:19]=2)[CH:5]=1)/[CH:40]=[CH:39]/[C:38]1[CH:37]=[CH:36][C:35]([NH:34][S:31]([CH3:30])(=[O:32])=[O:33])=[CH:45][CH:44]=1)([CH3:12])([CH3:13])[CH3:11]

Participants

3

Reactant 2

HCID 57775250(E)-4-(methylsulfonamido) styrylboronic acidHCID 668338485-(3-Bromo-5-tert-butyl-4-methoxyphenyl)-2,4-di-tert-butoxy-pyrimidine

Product 1

HCID 66833874(E)-N-(4-(3-tert-butyl-5-(2,4-di-tert-butoxypyrimidin-5-yl)-2-methoxystyryl)phenyl)methanesulfonamide

Procedure

The product from Example 2 Part A (55.9 mg, 0.12 mmol) and (E)-4-(methylsulfonamido) styrylboronic acid (28.9 mg, 0.120 mmol) were reacted in the same manner as Example 2 Step B. The crude product was purified by silica gel flash chromatography eluting with ethyl acetate/hexane (5% to 25%) to give the title compound.

Workup

  1. customThe crude product was purified by silica gel flash chromatography
  2. washeluting with ethyl acetate/hexane (5% to 25%)

Sources & evidence

ORD record
ord-180e3b4b26fd44c9a28bcf072b9cd136
Source dataset
uspto-grants-2014_06
Patent number
US08748443B2

Reaction notes

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