Potassium Phosphate, Tribasic → HCID 86710231, compound

HRID 2405914Notes

Reaction equation

HRID 2405914 reaction equation
I[C:2]1[CH:3]=[N:4][N:5]([CH2:7][CH2:8][C@@:9]([CH3:19])([S:15]([CH3:18])(=[O:17])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=1.[C:20]1(B(O)O)[CH2:24][CH2:23][CH2:22][CH:21]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:20]1([C:2]2[CH:3]=[N:4][N:5]([CH2:7][CH2:8][C@@:9]([CH3:19])([S:15]([CH3:18])(=[O:17])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=2)[CH2:24][CH2:23][CH2:22][CH:21]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 3861343(Cyclopent-1-en-1-yl)boronic acidHCID 70856733HCID 70856733, compound

Product 1

HCID 86710231HCID 86710231, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

Ethyl (2R)-4-(4-iodo-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)butanoate (100 mg, 0.25 mmol, 1 eq) was weighed into a 40 mL vial equipped with a septa cap. Cyclopent-1-en-1-ylboronic acid (97 mg, 0.5 mmol, 2 eq) and potassium phosphate (159 mg, 0.75 mmol, 3 eq) was added, followed by PdCl2(PPh3)2 (18 mg, 0.025 mmol, 0.1 eq). The vial was evacuated and backfilled 3 times with nitrogen gas. 2-MeTHF (9 mL) and water (1 mL) were added to the vial and the mixture heated at 100° C. overnight. The reaction mixture was then filtered through celite and eluted with MeOH. The crude product mixture was then purified by flash chromatography on a 25 g silicycle silica gel column eluting with 20% EtOAc/Hpt to give ethyl (2R)-4-[4-(cyclopent-1-en-1-yl)-1H-pyrazol-1-yl]-2-methyl-2-(methylsulfonyl)butanoate which was used without further purification. LC-MS M+H+341.4.

Workup

  1. customvial equipped with a septa cap
  2. customThe vial was evacuated
  3. addition2-MeTHF (9 mL) and water (1 mL) were added to the vial and the mixture
  4. filtrationThe reaction mixture was then filtered through celite
  5. washeluted with MeOH
  6. customThe crude product mixture was then purified by flash chromatography on a 25 g silicycle silica gel column
  7. washeluting with 20% EtOAc/Hpt

Sources & evidence

ORD record
ord-12c7944e6fd242b2b1141f3ca7fc7e9d
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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