Potassium Fluoride → HCID 67170310, compound

HRID 1475724Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1([NH:12][C:13]([C:15]2[CH:16]=[N:17][C:18]([O:22][CH3:23])=[C:19](Br)[CH:20]=2)=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[C:24]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)#[N:25].[F-].[K+].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1([NH:12][C:13]([C:15]2[CH:16]=[N:17][C:18]([O:22][CH3:23])=[C:19]([C:30]3[CH:29]=[CH:28][CH:27]=[C:26]([C:24]#[N:25])[CH:31]=3)[CH:20]=2)=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

The compound of step 2 (300 mg, 0.779 mmol), 3-cyano-phenylboronic acid (171 mg, 1.17 mmol), tris(dibenzylideneacetone)dipalladium(0) (214 mg, 0.234 mmol), potassium fluoride (149 mg, 2.57 mmol) and tri-tert-butylphosphonium tetrafluoroborate (136 mg, 0.47 mmol) in a flask were thoroughly flushed with argon, dioxane (3 ml) was added and the mixture was stirred for 2 h at 50° C. The mixture was filtered over silica gel and evaporated to dryness. This residue was purified by RP HPLC (water/ACN gradient) to yield 200 mg of the title compound.

Workup

additionwas added
filtrationThe mixture was filtered over silica gel
customevaporated to dryness
customThis residue was purified by RP HPLC (water/ACN gradient)

Sources & evidence

ORD record: ord-eaefe08e16ef4b40aba7c16b6e544ef2
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018383B2

Reaction notes

Loading…