Potassium Carbonate → HCID 178423464, compound

HRID 1842502Notes

Reaction equation

Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:22])[C:7]=1[N:8]1[CH2:11][CH:10]([C:12]2[NH:16][C:15]3[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:14]=3[N:13]=2)[CH2:9]1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:22][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:7]=1[N:8]1[CH2:11][CH:10]([C:12]2[NH:16][C:15]3[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:14]=3[N:13]=2)[CH2:9]1

Participants

Conditions

Temperature: 100 °C

Procedure

The mixture of 2-[1-(3,5-dichloro-pyridin-4-yl)-azetidin-3-yl]-5-methyl-1H-benzoimidazole (200 mg, 0.60 mol), phenylboronic acid (80 mg, 0.66 mmol), K2CO3 (166 mg, 1.2 mmol) and Pd(dppf)Cl2 (44 mg, 0.06 mmol) in toluene (10 mL) and H2O (3 mL) was stirred at 100° C. under N2 for 12 h. The mixture was then poured into H2O and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated to give the crude product and purified by column chromatography and followed by preparative HPLC to afford pure product 2-[1-(3-chloro-5-phenyl-pyridin-4-yl)-azetidin-3-yl]-5-methyl-1H-benzoimidazole (30 mg, 14%) as white solid. [M+1] 375. IC50 (uM) 0.022.

Workup

extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated
customto give the crude product
custompurified by column chromatography

Sources & evidence

ORD record: ord-e51554eb01fb46708f8e9490ab835c60
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946230B2

Reaction notes

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