Potassium Carbonate → 4-(4-((4'-Chloro-1,1'-biphenyl-2-yl)methyl)-1-piperazinyl)benzonitrile

HRID 731558Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

A solution of EXAMPLE 22C (932 mg, 2.591 mmol) in DMSO (13 mL) was treated with 4-fluorobenzonitrile (408 mg, 3.368 mmol) and K2CO3 (1.788 g, 12.955 mmol), heated at 130° C. for 4 hours, and filtered. The filtrate was partitioned between aqueous NaHCO3 and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined extracts were dried (MgSO4), filtered, and concentrated. The residue was purified by silica gel column chromatography with 20% ethyl acetate/hexanes to provide the desired product. MS (ESI) m/e 388, 390 (M+H)+.

Workup

filtrationfiltered
customThe filtrate was partitioned between aqueous NaHCO3 and ethyl acetate
extractionThe aqueous layer was extracted with ethyl acetate
dry with materialThe combined extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel column chromatography with 20% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-1f2cecdc350f4df384dccdf459c619e9
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585858B2

Reaction notes

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