Potassium Fluoride → 4-chloro-3-(4,6-dichloro-pyridin-3-yl)-N-[2-(2-dimethylamino-ethoxy)-phenyl]-N-methyl benzamide

HRID 1848582Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[C:5]([N:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[CH3:8])=[O:6].[F-].[K+].[Cl:27][C:28]1[CH:33]=[C:32]([Cl:34])[C:31](B(O)O)=[CH:30][N:29]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Cl:24][C:23]1[CH:22]=[CH:21][C:4]([C:5]([N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[CH3:8])=[O:6])=[CH:3][C:2]=1[C:31]1[CH:30]=[N:29][C:28]([Cl:27])=[CH:33][C:32]=1[Cl:34]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of dioxane (1.0 mL) containing 3-bromo-4-chloro-N-[2-(2-dimethylamino-ethoxy)-phenyl]-N-methyl-benzamide (44.0 mg, 0.11 mmol), Pd2(dba)3 (10 mg, 0.01 mmol), P(t-Bu)3HBF4 (7 mg, 0.022 mmol), KF (22 mg, 0.38 mmol) and 2,4 dichloropyridine-5-boronic acid (21 mg, 0.11 mmol) was degassed by bubbling N2 for 5 minutes and then sealed and heated at 110° C. overnight. The mixture was filtered and purified by preparative LCMS to yield 4-chloro-3-(4,6-dichloro-pyridin-3-yl)-N-[2-(2-dimethylamino-ethoxy)-phenyl]-N-methyl benzamide 7-1. MS [M+H]+: 478.0; tR=5.26 min. (method 2)

Workup

customwas degassed
customby bubbling N2 for 5 minutes
customsealed
filtrationThe mixture was filtered
custompurified by preparative LCMS

Sources & evidence

ORD record: ord-e89c5a3654bf48eb8869740571380ef7
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952161B2

Reaction notes

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