Sodium Carbonate → 2-{[(4-Fluorophenyl)methyl]oxy}-N-3-pyridinyl-5-(4-pyridinyl)benzamide

HRID 1623829Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:8].[N:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].B(O)O>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[F:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][O:17][C:5]2[CH:4]=[CH:3][C:2]([C:29]3[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=3)=[CH:16][C:6]=2[C:7]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}-N-3-pyridinylbenzamide (may be prepared as described in Example 59; 150 mg, 0.37 mmol) in 1,2-dimethoxyethane (5 ml) was added 4-pyridinylboronic acid (68.9 mg, 0.561 mmol), sodium carbonate (198 mg, 1.87 mmol) and bis(triphenylphosphine)palladium(II) chloride (15.74 mg, 0.02 mmol), followed by water (1 ml). The reaction was heated at 80° C. overnight. The reaction mixture was then placed in a microwave vial with another 0.5 eq of boronic acid and 5% catalyst and heated at 120° C. for 25 minutes. The solvent was removed in vacuo, redissolved in 1:1 DMSO/methanol and purified by MDAP to yield the title compound as white solid. 56 mg.

Workup

temperatureheated at 120° C. for 25 minutes
customThe solvent was removed in vacuo
dissolutionredissolved in 1:1 DMSO/methanol
custompurified by MDAP

Sources & evidence

ORD record: ord-298a97dab45e425b99570d8263b16933
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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