4-(Hydroxymethyl)benzeneboronic acid → 2-(4-(hydroxymethyl)phenyl)-N-methoxy-N-methylisonicotinamide

HRID 1909017Notes

Reaction equation

HRID 1909017 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][N:13]=1)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6].[OH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[CH:3]=[C:4]([CH:11]=[CH:12][N:13]=2)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 448186542-Bromo-N-methoxy-N-methylisonicotinamide

Product 1

HCID 866643442-(4-(hydroxymethyl)phenyl)-N-methoxy-N-methylisonicotinamide

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

By following procedures described in Example 32, starting from 2-bromo-N-methoxy-N-methyl-isonicotinamide and 4-hydroxymethyl phenyl boronic acid [but using Pd2(dba)3 instead of Pd(PtBu3)2], step 1 gave 2-(4-hydroxymethyl-phenyl)-N-methoxy-N-methyl-isonicotinamide.

Sources & evidence

ORD record
ord-e1c29e09dfa24ab88a0d5e9b683c4fda
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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