Potassium Fluoride → HCID 11500344, compound

HRID 2250528Notes

Reaction equation

HRID 2250528 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([CH3:12])[C:6](=[O:13])[C:5]2([CH3:15])[CH3:14].[CH3:16][N:17]1[C:21]([C:22]#[N:23])=[CH:20][CH:19]=[C:18]1B(O)O.[F-].[K+]>O1CCOCC1.CCOC(C)=O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[F:11][C:9]1[CH:10]=[C:2]([C:18]2[N:17]([CH3:16])[C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[CH:3]=[C:4]2[C:8]=1[N:7]([CH3:12])[C:6](=[O:13])[C:5]2([CH3:15])[CH3:14]

Participants

7

Reactant 3

HCID 522689Potassium FluorideHCID 11708078(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acidHCID 574399185-Bromo-7-fluoro-1,3-dihydro-1,3,3-trimethyl-2H-indol-2-one

Product 1

HCID 11500344HCID 11500344, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 178418851HCID 178418851, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

5-Bromo-7-fluoro-1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one (0.10 g, 0.36 mmol), 1-methyl-5-cyano-2-pyrroleboronic acid (95 mg, 0.63 mmol), KF (69 mg, 1.19 mmol) were suspended in 1 mL of dioxane. Pd2(dba)3 monochloroform adduct (3.1 mg, 0.003 mmol) and Pd(P(t-Bu)3)2 (4.6 mg, 0.009 mmol) were added and the mixture was stirred vigorously at 45° C. for 6 h. The mixture was diluted with 100 mL of EtOAc and filtered through a plug of silica gel and concentrated. Purification by flash chromatography (2% acetone/hexane) afforded the title compound (30 mg, 28%) as a tan solid.

Workup

  1. filtrationfiltered through a plug of silica gel
  2. concentrationconcentrated
  3. customPurification by flash chromatography (2% acetone/hexane)

Sources & evidence

ORD record
ord-4a5a540fffaa4d989af96121630b3b60
Source dataset
uspto-grants-2008_01
Patent number
US07317037B2

Reaction notes

Loading…