Sodium Carbonate → N-(3-Methoxyphenyl)-4-methyl-3-(3-piperidin-4-yl-1,2-benzisoxazol-6-yl)benzamide

HRID 1988919Notes

Reaction equation

HRID 1988919 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:27])[C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13](B3OC(C)(C)C(C)(C)O3)[CH:12]=2)[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:35]1[CH:49]=[CH:48][C:38]2[C:39]([CH:42]3[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]3)=[N:40][O:41][C:37]=2[CH:36]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:27])[C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([C:35]3[CH:49]=[CH:48][C:38]4[C:39]([CH:42]5[CH2:43][CH2:44][NH:45][CH2:46][CH2:47]5)=[N:40][O:41][C:37]=4[CH:36]=3)[CH:12]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 541219916-Bromo-3-piperidin-4-yl-1,2-benzisoxazoleHCID 59791522N-(3-Methoxyphenyl)-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide2×

Product 1

HCID 10478482N-(3-Methoxyphenyl)-4-methyl-3-(3-piperidin-4-yl-1,2-benzisoxazol-6-yl)benzamideYield 57%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

N-(3-Methoxyphenyl)-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (Intermediate 19, 54 mg), DME (3 ml), aqueous sodium carbonate (1M, 2 ml), tetrakis (triphenylphosphine) palladium (20 mg) and 6-bromo-3-piperidin-4-yl-1,2-benzisoxazole (44 mg) were heated together at 80° C. under nitrogen for 18 h. The solvent was evaporated and the residue was purified by column chromatography on silica (10 g) eluting with dichloromethane:ethanol:ammonia (40:8:1) to give the title compound (37 mg).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography on silica (10 g)
  3. washeluting with dichloromethane:ethanol:ammonia (40:8:1)

Sources & evidence

ORD record
ord-c2af617f5c0a491aa8a5bf724d33aa70
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

Loading…