Sodium Carbonate → 2-{[(4-Fluorophenyl)methyl]oxy}-5-(1-methyl-1H-pyrazol-5-yl)-N-3-pyridinylbenzamide

HRID 1623833Notes

Reaction equation

[CH3:1][N:2]1[C:6](B(O)O)=[CH:5][CH:4]=[N:3]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:26]=[N:27][CH:28]=[CH:29][CH:30]=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:38]=[CH:39][C:34]([CH2:33][O:32][C:20]2[CH:19]=[CH:18][C:17]([C:6]3[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=3)=[CH:31][C:21]=2[C:22]([NH:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[O:23])=[CH:35][CH:36]=1

Participants

Conditions

Temperature: 120 °C

Procedure

(1-Methyl-1H-pyrazol-5-yl)boronic acid (30.1 mg, 0.24 mmol), sodium carbonate (0.40 ml, 0.40 mmol) and tetrakis(triphenylphosphine)palladium(0) (13.82 mg, 0.01 mmol) were added to a solution of 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}-N-3-pyridinylbenzamide (may be prepared as described in Example 59; 80 mg, 0.20 mmol) in 1,2-dimethoxyethane (3 ml). The mixture was heated at 120° C. for 1 hour. The solvent was removed in vacuo and purified by MDAP to yield the title compound as a brown gum. 13 mg.

Workup

customThe solvent was removed in vacuo
custompurified by MDAP

Sources & evidence

ORD record: ord-aee760c86dfc45f89737e7d93b537733
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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