Potassium Phosphate, Tribasic → HCID 51038617, compound

HRID 1467932Notes

Reaction equation

HRID 1467932 reaction equation
[C:1](=[O:26])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[O:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:6]=[C:5]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH:4]=1.[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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:1](=[O:26])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[O:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:6]=[C:5]([C:14]2[CH:19]=[CH:18][C:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:16][CH:15]=2)[CH:4]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 51038404HCID 51038404, compound

Product 1

HCID 51038617HCID 51038617, compoundYield 90.5%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

1 mmol of 3-(4-bromophenyl)-1-(pyridin-2-yl)-1H-pyrazol-5-yl tert-butyl carbonate (21) prepared in Example B-2 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 (ethyl acetate)=5:1 (v/v)) to afford the title compound.

Workup

  1. additionwas charged in a 50 mL round-bottom flask
  2. filtrationAfter the solid was filtered through Celite
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. dissolutiondissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. concentrationconcentrated
  8. customThe resulting residue was purified by column chromatography (n-hexane:EA (ethyl acetate)=5:1 (v/v))

Sources & evidence

ORD record
ord-55d68540125741b7a00c338e1d04eead
Source dataset
uspto-grants-2015_04
Patent number
US09000176B2

Reaction notes

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