N-((6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-inden-3-yl)methyl)methanesulfonamide → N-((6-(3-tert-butyl-5-(2,4-di-tert-butoxypyrimidin-5-yl)-2-methoxy phenyl)-1H-inden-3-yl)methyl)methanesulfonamide

HRID 403667Notes

Reaction equation

HRID 403667 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].CC1(C)C(C)(C)OB([C:38]2[CH:46]=[C:45]3[C:41]([C:42]([CH2:47][NH:48][S:49]([CH3:52])(=[O:51])=[O:50])=[CH:43][CH2:44]3)=[CH:40][CH:39]=2)O1>>[C:10]([C:6]1[C:7]([O:8][CH3:9])=[C:2]([C:38]2[CH:46]=[C:45]3[C:41]([C:42]([CH2:47][NH:48][S:49]([CH3:52])(=[O:50])=[O:51])=[CH:43][CH2:44]3)=[CH:40][CH:39]=2)[CH:3]=[C:4]([C:14]2[C:15]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[N:16][C:17]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[N:18][CH:19]=2)[CH:5]=1)([CH3:12])([CH3:11])[CH3:13]

Participants

3

Reactant 2

HCID 57493915N-((6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-inden-3-yl)methyl)methanesulfonamideHCID 668338485-(3-Bromo-5-tert-butyl-4-methoxyphenyl)-2,4-di-tert-butoxy-pyrimidine

Product 1

HCID 66833976N-((6-(3-tert-butyl-5-(2,4-di-tert-butoxypyrimidin-5-yl)-2-methoxy phenyl)-1H-inden-3-yl)methyl)methanesulfonamide

Procedure

The product from Example 2 Part A (55.9 mg, 0.12 mmol) and N-((6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-inden-3-yl)methyl)methanesulfonamide (41.9 mg, 0.120 mmol) were reacted in the same manner as Example 2 Part 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-8f745a5f5f644bba9f139ebbca74f625
Source dataset
uspto-grants-2014_06
Patent number
US08748443B2

Reaction notes

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