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

HRID 1623828Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:17]1[CH:18]=[CH:19][C:20]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)=[C:21]([CH:31]=1)[C:22]([NH:24][C:25]1[CH:30]=[CH:29][N:28]=[N:27][CH:26]=1)=[O:23]>COCCOC.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>[F:40][C:37]1[CH:36]=[CH:35][C:34]([CH2:33][O:32][C:20]2[CH:19]=[CH:18][C:17]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[CH:31][C:21]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][N:28]=[N:27][CH:26]=2)=[O:23])=[CH:39][CH:38]=1

Participants

Conditions

Temperature: 120 °C

Procedure

4-Pyridinylboronic acid (81 mg, 0.66 mmol), sodium carbonate (1.09 ml, 1.09 mmol) and tetrakis(triphenylphosphine)palladium(0) (37.9 mg, 0.03 mmol) were added to a solution of 5-bromo-2-{([(4-fluorophenyl)methyl]oxy}-N-4-pyridazinylbenzamide (may be prepared as described in Example 77; 220 mg, 0.55 mmol) in 1,2-dimethoxyethane (5 ml). The reaction was heated at 120° C. for one hour. The solvent was removed in vacuo, redissolved in 1:1 dimethylsulfoxide/methanol and purified by MDAP to yield the title compound as a white solid. 58 mg.

Workup

customThe solvent was removed in vacuo
dissolutionredissolved in 1:1 dimethylsulfoxide/methanol
custompurified by MDAP

Sources & evidence

ORD record: ord-bdca2e06e84445d78e83c0e5900022dc
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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