Acetic Acid → HCID 86711540, compound

HRID 512499Notes

Reaction equation

Br[C:2]1[C:3](=[O:20])[C:4]([C:17]([OH:19])=[O:18])=[CH:5][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)[CH:7]=1.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1.C([O-])([O-])=O.[Cs+].[Cs+].C(O)(=O)C>O1CCOCC1>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:6]2[CH:7]=[C:2]([C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([C:22]([F:33])([F:32])[F:21])[CH:28]=3)[C:3](=[O:20])[C:4]([C:17]([OH:19])=[O:18])=[CH:5]2)=[CH:10][CH:11]=1)#[N:16]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 5-bromo-1-(4-cyano-benzyl)-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (preparation 12b, 0.56 g, 1.68 mmol), 3-(trifluoromethyl)phenylboronic acid (0.39 g, 2.05 mmol), 1,1′-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) (75 mg, 0.10 mmol) and Cs2CO3 (0.82 g, 2.51 mmol) in dioxane (4 mL) is heated for 24 h at 60° C. The reaction mixture is acidified with acetic acid and purified by preparative reversed-phase HPLC (Sunfire, gradient of methanol in water, 0.1% TFA, 60° C.). Yield: 186 mg (28% of theory); ESI mass spectrum: [M+H]+=399; Retention time HPLC: 1.22 min (Z002—002).

Workup

custompurified by preparative reversed-phase HPLC (Sunfire, gradient of methanol in water, 0.1% TFA, 60° C.)
custom1.22 min (Z002—002)

Sources & evidence

ORD record: ord-da478e273eb14b268a5e802733d93de4
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102624B2

Reaction notes

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