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

HRID 1988924Notes

Reaction equation

HRID 1988924 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7](=[O:24])[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10](B2OC(C)(C)C(C)(C)O2)[CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:32]1[CH:46]=[CH:45][C:35]2[C:36]([CH:39]3[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]3)=[N:37][O:38][C:34]=2[CH:33]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]([NH:6][C:2]2[S:1][CH:5]=[CH:4][N:3]=2)=[O:24])=[CH:9][C:10]=1[C:32]1[CH:46]=[CH:45][C:35]2[C:36]([CH:39]3[CH2:40][CH2:41][NH:42][CH2:43][CH2:44]3)=[N:37][O:38][C:34]=2[CH:33]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 219145174-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-N-(thiazol-2-yl)-benzamide2×HCID 541219916-Bromo-3-piperidin-4-yl-1,2-benzisoxazole

Product 1

HCID 99794304-Methyl-3-(3-piperidin-4-yl-1,2-benzisoxazol-6-yl)-N-(1,3-thiazol-2-yl)benzamideYield 70.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-N-(thiazol-2-yl)-benzamide (Intermediate 18, 50 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, 147 μmol) 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 (100:8:1) to give the title compound (43 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 (100:8:1)

Sources & evidence

ORD record
ord-ffd5e0a3ef044c6e9302965a3e6f9086
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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