4-Chlorophenylboronic acid → racemic 5-(4-chloro-phenyl)-N-(2-hydroxymethyl-butyl)-6-(3-methyl-isoxazol-5-ylmethoxy)-nicotinamide

HRID 1766518Notes

Reaction equation

HRID 1766518 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([OH:11])=O)[CH:5]=[N:6][C:7]=1Cl.[CH3:12][C:13]1[CH:17]=[C:16]([CH2:18][OH:19])[O:15][N:14]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.[NH2:30][CH2:31][CH:32]([CH2:35][CH3:36])[CH2:33][OH:34]>>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[C:7]([O:19][CH2:18][C:16]3[O:15][N:14]=[C:13]([CH3:12])[CH:17]=3)=[N:6][CH:5]=[C:4]([CH:3]=2)[C:9]([NH:30][CH2:31][CH:32]([CH2:33][OH:34])[CH2:35][CH3:36])=[O:11])=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 742994-Chlorophenylboronic acidHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 10820493(3-Methylisoxazol-5-yl)methanolHCID 153565332-(Aminomethyl)butan-1-ol

Product 1

HCID 11950062racemic 5-(4-chloro-phenyl)-N-(2-hydroxymethyl-butyl)-6-(3-methyl-isoxazol-5-ylmethoxy)-nicotinamide

Procedure

The title compound was synthesized in analogy to Example 75, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, 3-methyl-5-isoxazolemethanol, (4-chloro-phenyl)-boronic acid and 2-aminomethyl-1-butanol as starting materials to yield racemic 5-(4-chloro-phenyl)-N-(2-hydroxymethyl-butyl)-6-(3-methyl-isoxazol-5-ylmethoxy)-nicotinamide, MS (ISP) 430.3 (M+H)+.

Workup

  1. customThe title compound was synthesized in analogy to Example 75

Sources & evidence

ORD record
ord-9869a01739cf4fe696eb1f5f8b53910e
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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