Sodium Carbonate → N-[4-Methyl-3-(3-piperidin-4-yl-1,2-benzisoxazol-6-yl)phenyl]thiophene-3-carboxamide

HRID 1988920Notes

Reaction equation

HRID 1988920 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)=[O:10])=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.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>[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.CN(C=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)=[O:10])=[CH:4][C:3]=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 21914662N-[4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-thiophenecarboxamide2×HCID 541219916-Bromo-3-piperidin-4-yl-1,2-benzisoxazole

Product 1

HCID 10341918N-[4-Methyl-3-(3-piperidin-4-yl-1,2-benzisoxazol-6-yl)phenyl]thiophene-3-carboxamideYield 60.5%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

N-[4-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]thiophene-3-amide (Intermediate 15, 50 mg), DMF (1.5 ml), aqueous sodium carbonate (1M, 0.75 ml), tetrakis (triphenylphosphine) palladium (7.5 mg) and 6-bromo-3-piperidin-4-yl-1,2-benzisoxazole (41 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 (100:8:1) to give the title compound (36.8 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-b220efc905894a02bd3beca18acd77e3
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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