Sodium Carbonate → HCID 68516509, compound

HRID 1716299Notes

Reaction equation

HRID 1716299 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:10][N:11]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)[S:12]([CH3:15])(=[O:14])=[O:13])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[CH3:9][O:8][C:5]1[C:4]([CH2:10][N:11]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)[S:12]([CH3:15])(=[O:14])=[O:13])=[CH:3][C:2]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 68511606HCID 68511606, compound

Product 1

HCID 68516509HCID 68516509, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

A solution of N-(5-bromo-2-methoxy-pyridin-3-ylmethyl)-N-(4-p-tolyloxy-phenyl)-methanesulfonamide (0.16 g, 0.33 mmol) from Example 49 Step A and phenyl boronic acid (0.059 g, 0.49 mmol) in dioxane/H2O (2 mL/0.5 mL) was treated with Na2CO3 (0.11 g, 1.0 mmol) and PdCl2dppf.CH2Cl2 complex (23.8 mg, 0.033 mmol). The resulting mixture was heated at 100° C. overnight. The reaction mixture was brought to the usual work-up and the crude product was purified by chromatography (silica gel, 35% EtOAc/hexanes) to give the desired product. MS (EI) 475 (M+H)+.

Workup

  1. customthe crude product was purified by chromatography (silica gel, 35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ee8ddf6da517405891cf6d14faa505cc
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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