Potassium Carbonate → HCID 178509515, compound

HRID 1842495Notes

Reaction equation

Cl[C:2]1[C:3]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[NH:18][C:17]4[CH:19]=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:16]=4[N:15]=3)[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=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]>[C:25]1([C:2]2[C:3]([N:8]3[CH2:13][CH2:12][CH:11]([C:14]4[NH:18][C:17]5[CH:19]=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:16]=5[N:15]=4)[CH2:10][CH2:9]3)=[N:4][CH:5]=[CH:6][N:7]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 90 °C

Procedure

The mixture of 2-[1-(3-chloro-pyrazin-2-yl)-piperidin-4-yl]-1H-benzoimidazole-5-carbonitrile (160 mg, 0.47 mol), phenylboronic acid (69.3 mg, 0.57 mmol), K2CO3 (131 mg, 0.95 mmol) and Pd(dppf)Cl2 (34 mg, 0.047 mmol) in toluene (10 mL) and H2O (3 mL) was stirred at 90° C. under N2 for 12 h. Then it was poured into H2O and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated to give the crude product which was purified by column (ethyl acetate:petroleum ether=1:2) to give the compound 2-[1-(3-phenyl-pyrazin-2-yl)-piperidin-4-yl]-1H-benzoimidazole-5-carbonitrile (35 mg, yield 19.1%) as white solid. [M+1] 381. IC50 (uM) 0.272.

Workup

extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated
customto give the crude product which
customwas purified by column (ethyl acetate:petroleum ether=1:2)

Sources & evidence

ORD record: ord-a000803f67d94972a386bb1f51c57a82
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946230B2

Reaction notes

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