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

HRID 1988922Notes

Reaction equation

HRID 1988922 reaction equation
[CH:1]1([CH2:4][NH:5][C:6](=[O:23])[C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[C:9](B3OC(C)(C)C(C)(C)O3)[CH:8]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:31]1[CH:45]=[CH:44][C:34]2[C:35]([CH:38]3[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)=[N:36][O:37][C:33]=2[CH:32]=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>[CH:1]1([CH2:4][NH:5][C:6](=[O:23])[C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([C:31]3[CH:45]=[CH:44][C:34]4[C:35]([CH:38]5[CH2:39][CH2:40][NH:41][CH2:42][CH2:43]5)=[N:36][O:37][C:33]=4[CH:32]=3)[CH:8]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 21914588N-cyclopropylmethyl-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide2×HCID 541219916-Bromo-3-piperidin-4-yl-1,2-benzisoxazole

Product 1

HCID 10475463N-(Cyclopropylmethyl)-4-methyl-3-(3-piperidin-4-yl-1,2-benzisoxazol-6-yl)benzamideYield 50.3%

Reagents, catalysts & solvents 2

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

Procedure

N-Cyclopropylmethyl-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (Intermediate 21, 100 mg), DME (5 ml), aqueous sodium carbonate (1M, 3 ml), tetrakis (triphenylphosphine) palladium (0) (37 mg) and 6-bromo-3-piperidin-4-yl-1,2-benzisoxazole (76 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 70:8:1) to give the title compound (53 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 to 70:8:1)

Sources & evidence

ORD record
ord-55d5320b95d54299b2324b117356e3b5
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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