Potassium Fluoride → HCID 67091001, compound

HRID 2075697Notes

Reaction equation

HRID 2075697 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12][C:13]3[CH:14]=[C:15]([C:19]4([C:25]#[N:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH:16]=[CH:17][CH:18]=3)=[CH:9][CH:10]=2)[N:5]2[CH:27]=[N:28][N:29]=[C:4]2[CH:3]=1.[C:30]1([CH3:39])[CH:35]=[CH:34][CH:33]=[C:32](B(O)O)[CH:31]=1.[F-].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1COCC1.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]>[C:30]1([CH3:39])[CH:35]=[CH:34][CH:33]=[C:32]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([S:12][C:13]4[CH:14]=[C:15]([C:19]5([C:25]#[N:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]5)[CH:16]=[CH:17][CH:18]=4)=[CH:9][CH:10]=3)[N:5]3[CH:27]=[N:28][N:29]=[C:4]3[CH:3]=2)[CH:31]=1

Participants

7

Reactant 4

HCID 522689Potassium FluorideHCID 27339503-Tolylboronic acidHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 67090619HCID 67090619, compound

Product 1

HCID 67091001HCID 67091001, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

5s (70 mg, 0.17 mmol), m-tolylboronic acid (34 mg, 0.25 mmol), Pd2dba3 (4 mg, 0.01 mmol), potassium fluoride (29 mg, 0.50 mmol), and 2-(di-tert-butylphosphino)biphenyl (5 mg, 0.02 mmol) were dissolved in THF (5 mL) and degassed with N2 for 5 minutes. The reaction was heated to 80° C. for 5 hours, then cooled to room temperature and concentrated. The residue was purified by preparative HPLC to give the desired product, 5t.

Workup

  1. customdegassed with N2 for 5 minutes
  2. temperaturecooled to room temperature
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-845438884b2e44fdb714b9c6bc2bf0ed
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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