Potassium Fluoride → HCID 22730055, compound

HRID 2356119Notes

Reaction equation

HRID 2356119 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]#[N:11])=[C:7]([CH3:12])[C:6]=2[CH:13]=1.[CH3:14][O:15][C:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)=[O:17].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[F-].[K+]>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:10]([C:8]1[S:9][C:5]2[CH:4]=[CH:3][C:2]([C:21]3[CH:22]=[CH:23][C:18]([C:16]([O:15][CH3:14])=[O:17])=[CH:19][CH:20]=3)=[CH:13][C:6]=2[C:7]=1[CH3:12])#[N:11]

Participants

7

Reactant 4

HCID 522689Potassium FluorideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 27343694-Methoxycarbonylphenylboronic acidHCID 68452438HCID 68452438, compound

Product 1

HCID 22730055HCID 22730055, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 401A (557 mg, 2.68 mmol), (4-methoxycarbonylphenyl)-boronic acid (675 mg, 3.75 mmol), Pd(OAc)2 (36 mg, 0.16 mmol), 2-(di-tert-butylphosphino)biphenyl (63 mg, 0.21 mmol), and KF (467 mg, 8.04 mmol) in THF (10 mL) was heated to 60° C. for 16 hours and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexanes to provide the desired product.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-59a99b48103244f09a1187f132e269b1
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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