Toluene → HCID 66995524, compound

HRID 1160834Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].[C:7]1(C)C=CC=C[CH:8]=1.[C:14]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][C:21]=1[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)#[N:15].Cl[C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][N:40]=1)[C:35]([OH:37])=[O:36]>O.C(O)C>[C:14]([C:16]1[CH:17]=[C:18]([C:32]2[CH:33]=[C:34]([CH:38]=[CH:39][N:40]=2)[C:35]([O:37][CH2:7][CH3:8])=[O:36])[CH:19]=[CH:20][C:21]=1[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)#[N:15]

Participants

Conditions

Temperature: 100 °C

Procedure

6 ml of aqueous 2 M sodium carbonate solution and 70 mg of tetrakistriphenylphosphine palladium were added to a toluene (15 ml) solution of 450 mg of (3-cyano-4-pyridin-3-ylphenyl)boronic acid and 412 mg of 2-chloroisonicotinic acid, and in an argon atmosphere, this was heated at 100° C. for 2 hours. 3 ml of ethanol was added, followed by further heating at 100° C. for 1 hour. Water was added to the reaction mixture, followed by extraction with chloroform. The organic layer was washed with brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=99:1 to 93:7) to obtain 127 mg of ethyl 2-(3-cyano-4-pyridin-3-ylphenyl)isonicotinate. F: 330.

Workup

temperatureby further heating at 100° C. for 1 hour
extractionfollowed by extraction with chloroform
washThe organic layer was washed with brine
customdried
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (chloroform:methanol=99:1 to 93:7)

Sources & evidence

ORD record: ord-3aad4014db8d4247a9e4a3cb8a83f7b3
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816558B2

Reaction notes

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