Potassium Phosphate, Tribasic → HCID 58437493, compound

HRID 881643Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:31])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16](OS(C(F)(F)F)(=O)=O)=[C:17]([Cl:20])[CH:18]=3)[C:13]([C:29]#[N:30])=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2].[CH3:32]B1OB(C)OB(C)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:31])[C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([CH3:32])=[C:17]([Cl:20])[CH:18]=3)[C:13]([C:29]#[N:30])=[CH:12]2)=[CH:9][CH:10]=1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-(6-chloro-3-cyano-5-trifluoromethanesulfonyloxyindol-1-yl)benzoic acid ethyl ester (0.103 g), trimethylboroxine (0.033 g) and tripotassium phosphate (0.070 g) in dioxane (2.0 mL) was added tetrakis(triphenylphosphine) palladium catalyst (0.038 g), and this mixture was stirred at 80° C. for 1 day. The reaction mixture was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25) to give the title compound (0568 g).

Workup

customThe reaction mixture was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25)

Sources & evidence

ORD record: ord-4c099845aec94171b4165a4df30537b4
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993616B2

Reaction notes

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