Potassium Acetate → HCID 123213778, compound

HRID 718363Notes

Reaction equation

HRID 718363 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([O:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[N:6][CH:7]=1.CC1(C)C(C)(C)[O:22][B:21](B2OC(C)(C)C(C)(C)O2)[O:20]1.CC([O-])=O.[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]>[F:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][O:8][C:5]2[N:4]=[CH:3][C:2]([B:21]([OH:22])[OH:20])=[CH:7][N:6]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 118307774HCID 118307774, compound

Product 1

HCID 123213778HCID 123213778, compoundYield 39.7%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
85 °C

Procedure

A mixture of 5-bromo-2-(4-fluorophenethoxy)pyrimidine (200 mg), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (256 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (24.63 mg) and KOAc (198 mg) in 1,4-dioxane (8 mL) in a sealed tube was degassed with nitrogen for 2 minutes and then heated at 85° C. for 4 hours, followed by being stirred at room temperature for 24 h. The mixture was diluted with EtOAc, washed with water, brine, dried over MgSO4 and concentrated under vacuum. The residue was purified by silica gel column (Hex/EtOAc=10:1) to give (2-(4-fluorophenethoxy)pyrimidin-5-yl)boronic acid (70 mg). LCMS (M+H)=263.1.

Workup

  1. customwas degassed with nitrogen for 2 minutes
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica gel column (Hex/EtOAc=10:1)

Sources & evidence

ORD record
ord-8b074449efd84b4f9fae53e65d08ab9d
Source dataset
uspto-grants-2015_11
Patent number
US09193720B2

Reaction notes

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