1,4-Dioxane → HCID 51036477, compound

HRID 1467937Notes

Reaction equation

HRID 1467937 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([OH:13])[N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:9]=2)=[CH:4][CH:3]=1.[C:20]1([B:26](O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O1[CH2:42][CH2:41]OCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:2]1([C:42]2[CH:41]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([O:13][B:26]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 178515626HCID 178515626, compound

Product 1

HCID 51036477HCID 51036477, compound

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
100 °C

Procedure

1 mmol of 3-(4-iodophenyl)-1-(pyridin-2-yl)-1H-pyrazol-5-ol was charged in a 50 mL round-bottom flask and dissolved in 1,4-dioxane (10 mL), and phenylboronic acid (2.5 equivalents, manufactured by Aldrich) and K3PO4 (3 equivalents) were added thereto. Thereafter, PdCl2(dppf) (0.08 equivalents, manufactured by Aldrich) and dppf (1,1′-bis(diphenylphosphino)ferrocene, 0.04 equivalents, manufactured by Aldrich) were added thereto, followed by heating at 100° C. for 10 minutes. After the solid was filtered through Celite, the organic layer was concentrated under reduced pressure, dissolved in ethyl acetate and then washed with water. The organic layer was dried over anhydrous MgSO4 and concentrated. The resulting residue was purified by column chromatography (n-hexane:EA=8:1 (v/v)) to afford the title compound.

Workup

  1. filtrationAfter the solid was filtered through Celite
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography (n-hexane:EA=8:1 (v/v))

Sources & evidence

ORD record
ord-d084c2a24b1140a79d4185a924c9228c
Source dataset
uspto-grants-2015_04
Patent number
US09000176B2

Reaction notes

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